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  #1  
Old 07-22-2007, 11:15 PM
elelle elelle is offline
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How Exactly Are Drugs Made From Petroleum?

Perhaps my Google skills are weak, and I did a search here on the SD, but I cannot find a simple explaination of how drugs are made from petroleum oil. I searched because I was reading a harangue on "synthetic oil-based pharmaceuticals", and i just wondered how exactly they were made.

There's plenty of info about this substance and that, and testing of the purified chemicals, but I want to know the process from crude oil to pharmaceutical. How is it extracted?

I don't want this to become a harangue on the pharmaceutical industry, so don't go off on that; just asking for a simple decription of the process, and thought the better minds here could direct me towards the best info. Thanks.
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  #2  
Old 07-23-2007, 02:07 AM
Green Cymbeline Green Cymbeline is offline
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It sounds like you're referring to pharmaceuticals for external use, such as different lotions and creams which are made with pharmaceutical grade petrolatum or mineral oil (often used as bases for different topical medications). Also tar made from petroleum is used in topical medications for psoriasis.

Or are you talking about some type of internal medication?
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  #3  
Old 07-23-2007, 07:56 AM
HMS Irruncible HMS Irruncible is offline
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Quote:
Originally Posted by elelle
I don't want this to become a harangue on the pharmaceutical industry, so don't go off on that; just asking for a simple decription of the process, and thought the better minds here could direct me towards the best info. Thanks.
In the end, the drug industry is all about organic chemistry. Petroleum is a rich source of organics, and I suspect we'd synthesize everything from crude oil if it were viable. In fact many drug precursors probably come indirectly from petroleum, now that I think about it. A link to said harangue would be helpful. My whacko-sense tells me that this may be partly about linking two hated industry to create the shock value of "no blood for Prozac".
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Old 07-23-2007, 08:03 AM
chaoticbear chaoticbear is offline
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Originally Posted by Brain Wreck
In the end, the drug industry is all about organic chemistry. Petroleum is a rich source of organics, and I suspect we'd synthesize everything from crude oil if it were viable. In fact many drug precursors probably come indirectly from petroleum, now that I think about it. A link to said harangue would be helpful. My whacko-sense tells me that this may be partly about linking two hated industry to create the shock value of "no blood for Prozac".
As a followup, drug syntheses are usually pretty involved themselves, not to mention the failed attempts along the way, so it's pretty likely that something that you use to make the drug came from petroleum.
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  #5  
Old 07-23-2007, 08:37 AM
groman groman is offline
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Some basic Wikipedia articles:

Organic synthesis

Total synthesis

Petrochemicals
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  #6  
Old 07-23-2007, 02:16 PM
Solfy Solfy is offline
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Whee! A subject on which I can speak with a modicum of authority, having spent six years scaling up pharmaceutical intermediates.

Pharmaceuticals are typically large organic molecules. Large organic molecules are typically built by starting with small organic molecules and adding bits here and there, building them up and linking them as you go. I like to think of it as working with very tiny Legos.
Where do we get small organic molecules? Very frequently from refined petroleum. Crude oil is cracked and refined, a process by which the various small molecules get separated and sorted.
Additionally, linking these molecular bits is normally done in solution. Organic bits aren't water soluble for the most part, but rather in organic solvents. (methanol, ethyl acetate, heptane, toluene, etc.) Where do we get these organic solvents? Yep. Petroleum.

Sometimes the pharmaceutical itself has a "natural" origin. Take Taxol, for instance. It was isolated from a particular pacific yew. Simple! You say, round up the yew trees, collect Taxol, step 3 profit! No petroleum needed! Not so fast. There's very little taxol per yew. Add to that the fact that the Taxol was probably isolated by extracting from the yew via organic solvents. (pesky petroleum again) All the yew trees on the west coast wouldn't give you enough Taxol to make it marketable. Bring in the organic chemists and the petroleum based chemicals again. In this case they found a more abundant natural source that could be transformed to the chemotheraputic in a handful of steps, so it ended up being a natural/petro combo. More about Taxol here. Editing to add that close review of the link indicates that they're using a cell culture method for production now. Anyway, my point is still valid until they find a way to make superbugs spit out all the drugs.

This is why you can't really divide the molecules of the universe into "synthetic oil-based" and "natural." So called natural products can be made via synthetic means. This doesn't mean a completely synthesized Taxol molecule (it's been done from nearly scratch, IIRC) is any different from one that grew in the bark of a yew tree. A molecule is a molecule. But chances are if it's a designer molecule like a pharmaceutical, it's had some sort of petroleum derived history.

Last edited by Solfy; 07-23-2007 at 02:18 PM..
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Old 07-23-2007, 08:27 PM
elelle elelle is offline
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Thanks for all replies, and especially Solfy; your reply helped me understand the process better. The example of Taxol is a good one; I'm familiar with that story, know one of the pharmacognocists involved with the breakthrough of taxus species as usable.

I did go to Wiki first to try to understand where the origin of drugs in manufacture, and it just wasn't clear. So, Solfy, since you have the good experience; petroleum is refined and broken down into it's components, and then the purified substance is distributed to pharmaceutical companies for research and development. The harangue I read was pretty out there, and I don't agree with it. "All synthetic petrochemicals are poison," yadda yadda. I'm for medicine that helps people.

But, I was also struck by the fact that I could not find a simple explaination online where drugs come from at the source. The specifics might be proprietary, but the basics of extraction from petroleum sources would seem to be something everyone would want to know, in the manner of "this is where we are with medicine".
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Old 07-23-2007, 08:50 PM
633squadron 633squadron is offline
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Quote:
Originally Posted by elelle
But, I was also struck by the fact that I could not find a simple explaination online where drugs come from at the source. The specifics might be proprietary, but the basics of extraction from petroleum sources would seem to be something everyone would want to know
Except that it's misleading to say that we "extract" drugs from petroleum. We extract quinine from the bark of a tree found in the Philippines. We may extract some sort of pharmaceutical from petroleum, but one does not come to mind offhand.

Most of the stuff we use in or on our bodies are mixtures of ingredients. An ingredient may be extracted in its final form from something in nature. It can also be synthesized in a chemical reaction from basic building blocks; the building blocks are what are extracted from nature.

A fun and ironic example is aniline dye. Its discoverer was looking for an artificial source of quinine in coal tar; instead, he produced a easily-used dye that produced a wonderful purple color. It is the forerunner of all modern dyes. He extracted part of the dye from coal tar, and combined it in a chemical reaction with other building blocks to get the final product.

Did he extract aniline dye from coal tar? You could say that, but it would be a bit misleading.

Same goes for pharmaceuticals. We may get some of the basic building blocks from oil. This goes beyond my memory, but I think we may synthesize some of the amines that go into sulfa drugs from basic molecules we get from petroleum. We do not get amines directly from petroleum!

The most likely ingredient from petroleum is likely to be an oil or ointment used in an externally-applied pharm. Neosporin, for example, uses petrolatum (aka Vaseline) which comes from petroleum. It was, in fact, first discovered in the first oil wells!

In fact, the active ingredient in most pharmaceuticals these days is likely to be some sort of natural product that we do in fact extract from a plant or animal.
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Old 07-23-2007, 08:52 PM
HMS Irruncible HMS Irruncible is offline
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Quote:
Originally Posted by elelle
But, I was also struck by the fact that I could not find a simple explaination online where drugs come from at the source. The specifics might be proprietary, but the basics of extraction from petroleum sources would seem to be something everyone would want to know, in the manner of "this is where we are with medicine".
Why? Medicine is so far removed from petroleum that it's like observing that our bodies are made of the fusion of dying stars, and wondering if we might not shine light out of our butts. It's so far removed that it's virtually irrelevant.

Besides, it's not as if these medicines could only have been made of petroleum. The basic building blocks exist in every living thing, in slighly more assembled format. It just turns out that the basic forms exist in the greatest quantities in petroleum.
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Old 07-23-2007, 09:06 PM
Squink Squink is offline
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Quote:
Originally Posted by 633squadron
We may extract some sort of pharmaceutical from petroleum, but one does not come to mind offhand.
Mineral oil was a miracle laxative in its day.
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  #11  
Old 07-23-2007, 09:19 PM
elelle elelle is offline
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Quote:
Originally Posted by Brain Wreck
Why? Medicine is so far removed from petroleum that it's like observing that our bodies are made of the fusion of dying stars, and wondering if we might not shine light out of our butts. It's so far removed that it's virtually irrelevant.

Besides, it's not as if these medicines could only have been made of petroleum. The basic building blocks exist in every living thing, in slighly more assembled format. It just turns out that the basic forms exist in the greatest quantities in petroleum.
OK, I hear you, but please elaborate on it. From what Solfy posted, many pharmaceuticals are derived from petroleum. Is that true, or are there other sources, and what are they? I'm just looking for simple answers/
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Old 07-24-2007, 10:07 AM
Solfy Solfy is offline
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Quote:
Originally Posted by elelle
OK, I hear you, but please elaborate on it. From what Solfy posted, many pharmaceuticals are derived from petroleum. Is that true, or are there other sources, and what are they? I'm just looking for simple answers/
I fear I have misled you. We don't extract the pharmaceuticals from petroleum. We extract many of the small molecules needed to assemble the pharmaceuticals from petroleum.
Going back to Taxol, since it's a great example - we extract the precursor molecule from tree bark. Probably we extract that using a petrochemical solvent (I could be wrong - this isn't the end I work on). Mash up tree bark, pour solvent over it, precursor dissolves in solvent, filter off bits of leftover tree. Strip off solvent, collect precursor. (along with a whole host of other organic molecules which now have to be separated out)
Take your drug precursor and manipulate it chemically. Frequently these chemical manipulations are done in petrochemically derived solvents, possibly with petrochemically derived reagents (but not necessarily). These manipulations switch out and/or add different bits of the molecule until you've got the Taxol molecule. The pharmaceutical didn't come from petroleum, but it was made with the assistance of petroleum-sourced products.

You are correct in questioning the "all synthetic petrochemicals are poison" bit. Methylene chloride (a common solvent) would not be a good thing to drink. However, it's a useful solvent to disovle organic molecules, react them with other molecules, and isolate. Is there methylene chloride in the final product? Not if you've isolated it correctly. Is methylene chloride useful? Yes! It would be next to impossible to do organic chemistry without petrochemicals. This does NOT mean pharmaceuticals are floating around in the crude oil waiting for us to gather them.

Where to find pharmaceutical molecules is BIG business. People are constantly isolating secrections from leaches, bits of sea sponges, compounds from pepper plants, horomones from horse urine. The world is made of molecules, and some of them are handy for treating diseases. It's a matter of finding the molecules that are useful, verifying their usefullness, verifying that they are not harmful in ways that negate their usefulness, and finding a way to mass produce them.
When it comes down to it, no matter how you've mass produced a molecule, it's still just a molecule no matter what its origin.
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Old 07-24-2007, 10:36 AM
Outpits Outpits is offline
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Quote:
Originally Posted by 633squadron
In fact, the active ingredient in most pharmaceuticals these days is likely to be some sort of natural product that we do in fact extract from a plant or animal.
It is very misleading to say that most, even many, recently introduced pharmaceuticals are some sort of natural product extracted from natural sources. While this was closer to true at one time (e.g., antibiotics and hormones), science has changed so much that natural products are rarely acceptable as drugs. There are some cases where a natural ligand to a receptor or an antibody can be the starting point for drug development, but medicinal (organic) chemists will modify it to improve many of its properties (e.g., the way it is metabolized in the body, its size, its immunogenicity for an injectable, its solubility, its absorption). The "starting point" is often not even recognizable in the end product that results from these changes.

None of the compounds on the top ten worldwide best selling drugs are in any way, shape, or form natural product extracts.

Even many biological products (e.g., new insulin analogs, antibodies) are modified to improve their biological properties or their manufacturability properties. Almost all the modern bioproducts are produced in recombinant bacteria or yeast so there is some modification to suit their manufacturing.

Last edited by Outpits; 07-24-2007 at 10:37 AM..
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  #14  
Old 07-24-2007, 11:27 AM
groman groman is offline
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Quote:
Originally Posted by elelle
OK, I hear you, but please elaborate on it. From what Solfy posted, many pharmaceuticals are derived from petroleum. Is that true, or are there other sources, and what are they? I'm just looking for simple answers/
Well, you can use several methods to destroy longer organic chains to turn them into petroleum (or to be more precise, petroleum-like product, since petroleum generally refers to the substances occurring naturally). Basically you can take biological matter, like human and animal carcasses, vegetable matter, etc. and turn it into crude oil, then you can use roughly the same process to derive pharmaceuticals as we do now.
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Old 07-24-2007, 02:15 PM
Andy Andy is offline
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I wonder if this analogy might help. The mouse in your hand, if mostly plastic, could be said to be derived from petroleum. Cracking of petroleum to something like ethylene and then polymerisation led to the plastic used in the case and many of its components. However, the complexity of a mouse is far removed and unrelated to what is found in petroleum. Mice are not found in petroleum but it does play a vital role in their manufacture.
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Old 07-24-2007, 02:30 PM
HMS Irruncible HMS Irruncible is offline
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Quote:
Originally Posted by elelle
OK, I hear you, but please elaborate on it. From what Solfy posted, many pharmaceuticals are derived from petroleum. Is that true, or are there other sources, and what are they? I'm just looking for simple answers/
Please understand you are looking for simple answers to a complex question. There is only so much that this can be simplified.

To take one example, one of the commonest simple building blocks of pharmaceutical compounds is the benzene ring. These are found in virtually every living thing (for example, the amino acid phenylalanine), and they are ubiquitous in pharmaceuticals as welll (for example Prozac). If you look at the structures of all those molecules you see a benzene ring. If you were to try to get a free benzene ring from animal or plant sources, you'd have to do some work to break it down to the basic form. It just so happens that petroleum has a significant fraction of free benzene... why? Because it's made of dead life-forms, nature has already broken it down for us. So it makes the most sense to source it from there.

Last edited by HMS Irruncible; 07-24-2007 at 02:32 PM..
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Old 07-24-2007, 06:39 PM
scm1001 scm1001 is offline
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To elaborate a bit more in a simplistic way .

Petrol based products are initially just carbons and hydrogens stuck together in rings and chains (about 10-40 atoms). Good for burning, but not water soluble and only dont really interact or affect people much.

To create biological relevant drugs you need to stick lots of oxygens, nitrogens and sulfurs on them. This makes them more water soluble and give points of biochemical reaction/interaction. Thats what the organic chemist does, as well as making them bigger often. It might take 40 reactions to turn a raw petrochemical into Taxol, or perhaps 2-3 into something simple like asprin.

There are many chemicals than can be derived from animals or plant sources used for drug manufacture too (e.g. aspirin). In many cases both petroleum or natural chemicals are similarly priced, but usually one or the other is much cheaper. The petroleum and naturally derived chemicals will be identical in all ways and one will not be better or worse for you.
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Old 07-24-2007, 07:34 PM
elelle elelle is offline
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Thanks greatly for the above posts, they have clarified the process for me. I was using the term"extract" to mean "made from", and I see now that it is a more specific term in chemistry, as opposed to synthesizing molecules from a source.

Brain Glutton, this was very helpful:
Quote:
If you were to try to get a free benzene ring from animal or plant sources, you'd have to do some work to break it down to the basic form. It just so happens that petroleum has a significant fraction of free benzene... why? Because it's made of dead life-forms, nature has already broken it down for us. So it makes the most sense to source it from there.
Thanks again to all for the help in understanding.
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Old 11-15-2010, 03:15 PM
Peace Hemp Peace Hemp is offline
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Originally Posted by Solfy View Post
This is why you can't really divide the molecules of the universe into "synthetic oil-based" and "natural." So called natural products can be made via synthetic means. This doesn't mean a completely synthesized Taxol molecule (it's been done from nearly scratch, IIRC) is any different from one that grew in the bark of a yew tree. A molecule is a molecule.
Hi, Solfy,

Actually, these statements are not as true as they sound. Naturally-occurring compounds are not necessarily the same as their synthetic counterparts, despite being EXACT CHEMICAL DUPLICATES. They do not bear the same properties and they do not have the same effects.

Take Marinol, for example. It is delta-9-tetrahydrocannabinol. In every scientific definition, Marinol is the mirror image of the natural compound found in Cannabis Sativa L., but numerous studies have shown that the effect of the synthetic Marinol are not only not the same, but far inferior to the natural form found in the wild. It can't be explained in scientific terms, outside of the statement: "results are not typical and are, therefore, unreliable."

It's an insurance policy, so to speak, established by Mother Nature (God, All That Is, Brahma, Light, The Universe, The Great Unconscious, Etc) to prevent humans from synthesizing their way out of a balanced, natural world.

In other words, it is the Universe keeping us from "playing God".

A thing can be proven through the scientific method, but that does not mean it can be successfully replicated. ~Brian Reymore
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Old 11-16-2010, 01:51 AM
2square4u 2square4u is offline
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Originally Posted by Peace Hemp View Post
Naturally-occurring compounds are not necessarily the same as their synthetic counterparts, despite being EXACT CHEMICAL DUPLICATES. They do not bear the same properties and they do not have the same effects.

Take Marinol, for example. It is delta-9-tetrahydrocannabinol. In every scientific definition, Marinol is the mirror image of the natural compound found in Cannabis Sativa L., but numerous studies have shown that the effect of the synthetic Marinol are not only not the same, but far inferior to the natural form found in the wild.
You are making a fundamental error in your reasoning.

The "mirror image" cannot be an "exact chemical duplicate". If it were an exact chemical duplicate, it wouldn't be the mirror image, it would be the compound itself.

Quote:
Dronabinol is the International Nonproprietary Name (INN) for a pure isomer of THC, (-)-trans-Δ9-tetrahydrocannabinol, that is, the main isomer in cannabis. It is sold as Marinol (a registered trademark of Solvay Pharmaceuticals)
Quote from Wikipedia, bolding mine. Some organic molecules exist in different isomers (mirror images), and it's well known that the biological effects of one isomer may differ from the the biological effects of the other isomer. A competent chemist with the appropriate tools is perfectly able to distinguish analytically between two different isomers of the same compound.

Another example is the molecule vanillin. Vanillin can be synthesized from petroleum-based precursors or from the natural lignin in wood. Provided sufficient purity of the sample, no-one will be able to tell you where that vanillin came from. However, wood-based vanillin is more popular as a flavoring compound in foods, because it's (irrationally) regarded as more "natural", while petrochemical-based vanillin is preferred as a precursor for medical drugs, since it's actually easier to produce in sufficient purity for the pharmaceutical industry

Short version of the above: If the synthetic molecule is an exact chemical duplicate, no-one, neither Nature nor the analytical chemist will be able to tell whether the molecule is of "natural" or "synthetic" origin.
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Old 11-16-2010, 04:29 AM
Busy Scissors Busy Scissors is offline
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Originally Posted by 2square4u View Post
You are making a fundamental error in your reasoning.

The "mirror image" cannot be an "exact chemical duplicate". If it were an exact chemical duplicate, it wouldn't be the mirror image, it would be the compound itself.

Quote from Wikipedia, bolding mine. Some organic molecules exist in different isomers (mirror images), and it's well known that the biological effects of one isomer may differ from the the biological effects of the other isomer. A competent chemist with the appropriate tools is perfectly able to distinguish analytically between two different isomers of the same compound.

Another example is the molecule vanillin. Vanillin can be synthesized from petroleum-based precursors or from the natural lignin in wood. Provided sufficient purity of the sample, no-one will be able to tell you where that vanillin came from. However, wood-based vanillin is more popular as a flavoring compound in foods, because it's (irrationally) regarded as more "natural", while petrochemical-based vanillin is preferred as a precursor for medical drugs, since it's actually easier to produce in sufficient purity for the pharmaceutical industry

Short version of the above: If the synthetic molecule is an exact chemical duplicate, no-one, neither Nature nor the analytical chemist will be able to tell whether the molecule is of "natural" or "synthetic" origin.
Nice post to correct the cabbagery immediately above. Mirror image, such a loaded term
Minor nitpick - You can in fact discriminate between natural and synthetic molecules, through isotope distributions. This is done in the flavours and fragrance industry for things like jasmine. As you point out, the naturally sourced substance commands a premium in marketing terms.
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Old 11-16-2010, 05:16 AM
Nava Nava is offline
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Originally Posted by elelle View Post
OK, I hear you, but please elaborate on it. From what Solfy posted, many pharmaceuticals are derived from petroleum. Is that true, or are there other sources, and what are they? I'm just looking for simple answers/
Coal, natural gas, mines, for the smallest molecules which are then cooked into different molecules and these into different molecules and these... and then these mixed with other molecules, packaged and sent to the pharmacy; also, for items whose atoms don't end up in the final product but which are necessary in between (mineral acids, catalysts, solvents... sulphuric acid is made from sulphur, which is an "undesirable but economically valuable residue" from refineries, so even though it's a mineral acid and not an organic substance, it ends up coming from petroleum, gas or coal too; it is used in lots of organic reactions).

Vegetal and animal sources, for other "lego blocks" which are more complicated than the ones extracted from oil, coal or natural gas.

For example, one "inert" compound often found in pills is glucose, which is cheaper to get from vegetable sources than to cook from oil; the active ingredient (say, o-acetyl-salicylic acid) is more likely to have ultimately come from an oil well (and this from ancient trees) than to have been extracted from a plant (and I have purposefully chosen an active ingredient which can be extracted from plants, it just happens to be much more efficient to cook it, with modern technology).

Note that this applies to pretty much anything around you. Plastics. Your clothing. I'm wearing panties which are mostly cotton (a fiber obtained from a plant) with a bit of spandex (a fiber cooked from petroleum), and the dyes could be made from petroleum, obtained from vegetal or animal sources, or a mixture of dyes from several origins.


ETA: the isotope distribution thing was used at least once to detect wines to which alcohol synthesised from petroleum had been added.

Last edited by Nava; 11-16-2010 at 05:20 AM..
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Old 11-16-2010, 05:34 AM
Slightly mad scientist Slightly mad scientist is offline
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You can distinguish them in the laboratory, but the chemistry and biology of a natural and a synthesized compound are essentially indistinguishable. If your compounds behave differently in chemical or biological tests, then they are different compounds.

Chemical compounds isolated from natural sources are also synthesized out of smaller building blocks. Nature is much better than we at synthesizing complex chemicals selectively, but the resulting compounds are the same as those synthesized in a lab. There is no mysterious property of natural compounds that makes them behave differenty that we don't understand.

I'm repeating the previous answers here, but this is a very important point: The mirror image of a molecule (enantiomer) is a different molecule! They behave differently biologically, chemically and even physically. You can distinguish them easily by observing how they rotate polarized light.
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Old 11-16-2010, 06:44 AM
Ruken Ruken is offline
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Originally Posted by 2square4u View Post
Another example is the molecule vanillin. Vanillin can be synthesized from petroleum-based precursors or from the natural lignin in wood. Provided sufficient purity of the sample, no-one will be able to tell you where that vanillin came from. However, wood-based vanillin is more popular as a flavoring compound in foods, because it's (irrationally) regarded as more "natural", while petrochemical-based vanillin is preferred as a precursor for medical drugs, since it's actually easier to produce in sufficient purity for the pharmaceutical industry
"Natural" vanilla extract is also not a pure solution of vanillin in ethanol/water. Many of the impurities have noticeable (and potentially desirable) flavors. Now I certainly can't tell the difference, but I knew a guy who could double blind identify vanilla and cinnamon (mostly cinnamaldehyde). Likewise, the active ingredient in Marinol, while the major psychoactive component in cannabis (and not a different enantiomer or diasteriomer) is not the only psychoactive component, so we shouldn't expect the effects to be identical (never mind that the delivery method is different as well).
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Old 11-16-2010, 07:21 AM
Ruken Ruken is offline
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Originally Posted by Ruken View Post
Now I certainly can't tell the difference, but I knew a guy who could double blind identify vanilla and cinnamon (mostly cinnamaldehyde).
I wrote that wrong. He could identify different sources of vanilla and cinnamon.
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