3,4-divanillyltetrahydrofuran query

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    Basically there is no such thing as 95% we found via quite a few detailed lab tests. While it is still more more unique and expensive over a plain Nettle Extract it has a lot of oligimers and not a 95% of that single lignand. More info here and this goes for any product with "Divanil":

    In an effort to provide top-quality products and accurate labeling, Anabolic Xtreme recently partnered with ThermoLife to examine a potential problem with one of AX’s ingredients, 3,4-divanillyltetrahydrofuran.

    While AX began formulating a new version of MASS-FX, they encountered similar problems testing one of the ingredient characterized by it’s founders (DS) as 95% 3,4-divanillyltetrahydrofuran (3,4-D). As a result, AX turned to ThermoLife, which has one of most stringent quality control and testing programs in the industry.

    ThermoLife and AX commissioned an independent lab to analyze all the material in the market for this specific compound to obtain proper identification. After extensive tests, botanical analysis, and chromograph fingerprints, the material was identified to have a purity of less than 5% 3,4-D, no illegal steroidal structures, and to stem from the Urtica diocia (Nettle) botanical family. The testing procedure was repeated for several additional samples from every known supplier and various products on the market labeled 95% 3,4-D. All of the tests reached the same conclusion of less than 5% 3,4-D purity.

    While confident that the ingredient formerly known as 3,4-D “works,” due to the enormous amount of consumer feedback and the Mass-FX University study, the information provided from the results of ThermoLife’s independent market analysis of the compound has responsibly led AX to change its labels to identify the material as “a proprietary extract of the Urtica dioca plant” to comply with federal labeling regulations.

    “We are very happy to have the correct label information for this ingredient,” noted Steve Bonnell, Chief Operations Officer of AX. “ThermoLife’s testing helped reveal a purity misrepresentation, and now we can be sure we are providing correctly indentified products for our loyal customers,” he added.

    According to third party testing companies, more than a quarter of finished dietary supplement products sold in the US, and as much as 85% of certain ingredients, have been adulterated or mislabeled in some way. As a result of the 3,4-D testing, AX has pledged to employ several new quality control procedures that range from adulteration and contamination testing to additional material screenings. AX aims to expand its quality assurance testing and develop the highest quality products in the industry.
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    Quote Originally Posted by AthleticXtrem View Post
    After extensive tests, botanical analysis, and chromograph fingerprints, the material was identified to have a purity of less than 5% 3,4-D, no illegal steroidal structures, and to stem from the Urtica diocia (Nettle) botanical family. The testing procedure was repeated for several additional samples from every known supplier and various products on the market labeled 95% 3,4-D. All of the tests reached the same conclusion of less than 5% 3,4-D purity.

    While confident that the ingredient formerly known as 3,4-D “works,” due to the enormous amount of consumer feedback and the Mass-FX University study, the information provided from the results of ThermoLife’s independent market analysis of the compound has responsibly led AX to change its labels to identify the material as “a proprietary extract of the Urtica dioca plant” to comply with federal labeling regulations.

    “We are very happy to have the correct label information for this ingredient,” noted Steve Bonnell, Chief Operations Officer of AX. “ThermoLife’s testing helped reveal a purity misrepresentation, and now we can be sure we are providing correctly indentified products for our loyal customers,” he added.
    Let me see if I understand this correctly. Are you stating that all products, and sources industry wide, of the same test at <5% purity including yours?

    You are not claiming that yours has a higher purity but rather you are stating (via disclaimer) that yours is a “a proprietary extract of the Urtica dioca plant”?

    You are also stating that any other claims of any other products manufacturers are unfounded and that they are actually of equal or less than (<5% 3,4-D) the purity standard that you have revealed in testing?

    So what you're saying is there are none, including your own, greater than 5% of 3,4-D? Is this correct?
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    That is correct. We have tested every single product that is supposed to have a 95% just to see if it were possible and they all came back at less than 5%. Some at less than 1%. That being said if you take the spectrum of NOW nettle extract and compare it to this proprietary extract it is very different. The peaks suggest their are multiple oligimers and lignands in this extract with 5% being the 3,4. It was over $15k in testing that was done with Chromadex to confirm this.

    There is not a single product that will test at 95% (and none over 5%). We have a pure standard at Chromadex anyone can now test against. Until this was done, no one had paid to have the material really examined in detail. The give away is the color. The 3,4D on the market has a dark brown extract quality where something that is 95% pure would be white or off white like the reference standard that was created by Chromadex.
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    Quote Originally Posted by AthleticXtrem View Post
    That being said if you take the spectrum of NOW nettle extract and compare it to this proprietary extract it is very different. The peaks suggest their are multiple oligimers and lignands in this extract with 5% being the 3,4.
    I'm unclear on what you are implying about the Now brand nettle extract. I assume you are suggesting that there are multiple oligimers and lignands with only 5% being 3,4. Correct?

    So when NutraPlanets states: "Stinging Nettle Root: Wide Spectrum Stinging Nettle Root Extract Including 3,4-divanillyltetrahydrofuran" they are "stating" a wide spectrum (other oligimers and lignands) in addition to the presence of 3,4-divanillyltetrahydrofuran.

    What I don't understand is why this has not yet been synthesized for 100% pure 3,4 extract in the same way Syntrax synthesized the E and Z Guggulsterone in their Guggul Extract?
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    I guess I am not explaining it well and could have the professor come over to explain a bit better. NOW foods is a very crude extract with nothing special in it, the UADX/Divanil is concentrated extract that I still think is worth the price . NOW and other nettle is about $18/kg where the UADX/Divanil is about $250/kg to produce.

    A pure form of 3,4D was investigated however it would run about 10k a kg . Meaning a bottle would be a few hundred dollars minimum. Not really worth it as no one would pay that amount for the supplement.
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    The expense being the cost to synthesize such a pure form? I am wondering if this cost will come down at some point??

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    Quote Originally Posted by ryansm View Post
    The expense being the cost to synthesize such a pure form? I am wondering if this cost will come down at some point??
    It would take a while and a lot of volume. I just don't see it being feasible for a company to have a $350 product that has 500mg a day of pure 3,4. No one would buy it, and no other companies would follow lead. Trust me it has been investigated heavily and is a very long process to create hence the expense.

    It's often a balance of innovation and what the market will bear. We research many compounds that need to be purified from an extract or synthesized and 70% of the time, the market would just not bear the price.

    However we are beginning testing after a successful synth of a pure testosterone mimitec that has never been seen before. It's been two years in the works and could be the biggest product we have ever come out. It will still be expensive but the market could bear it for this product.
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    Quote Originally Posted by AthleticXtrem View Post
    I guess I am not explaining it well and could have the professor come over to explain a bit better. NOW foods is a very crude extract with nothing special in it, the UADX/Divanil is concentrated extract that I still think is worth the price . NOW and other nettle is about $18/kg where the UADX/Divanil is about $250/kg to produce.

    A pure form of 3,4D was investigated however it would run about 10k a kg . Meaning a bottle would be a few hundred dollars minimum. Not really worth it as no one would pay that amount for the supplement.
    No, you are explaining it very well. I'm just repeating what you are saying to help myself understand. NOW brand being more crude was how I interpreted it. I just wanted to confirm I was getting what you were saying.

    Thank you very much for the very comprehensive and informative replies.
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    If things had been this concise originally I wouldn't have had to spend 30 minutes reading the thread over at BB.com lol. Having no drama in the thread is very helpful.
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    all these companies has the same thing they have always had they just dont call it 95 any more? then who really cares as long as were getting the same gainz?
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    Quote Originally Posted by f1tjunkie View Post
    all these companies has the same thing they have always had they just dont call it 95 any more? then who really cares as long as were getting the same gainz?
    I for one care. There are too many variables to the anecdotal evidence of gains. It's not always about the gains.

    There are only a few scholarly journals on this ingredient because sadly none are free, however they do note 3,4-Divanillyltetrahydrofuran binding affinity for SHBG. In one journal they state "All lignans except (-)-pinoresinol developed a binding affinity to SHBG in the in vitro assay. The affinity of (-)-3,4-divanillyltetrahydrofuran was outstandingly high" (1). Another journal says the same, "Lignans bind to sex hormone-binding globulin (SHBG). The lignan with the greatest binding affinity is (+/-)-3,4-divanillyltetrahydrofuran" (2). Although we aren't able to see the actual research done, this information from the abstract does state that 3,4-divanillyltetrahydrofuran attaches to SHBG. This shows that the claims are true, however to what extent is not known. Many people have ran sponsored/unsponsored logs of products with this ingredient and also had blood tests done showing free testosterone before and after, so if you would like to see some anecdotal feedback you could find those online.

    References:
    1. Schottner, M., G. Gansser, and D. Spiteller. "Lignans from the roots of Urtica dioica and their metabolites bind to human sex hormone binding globulin (SHBG)." Planta Med. 63 (1997): 529-32. PubMed.

    2. Schöttner, M., D. Gansser, and G. Spiteller. "Interaction of lignans with human sex hormone binding globulin (SHBG)." Z Naturforsch C. 52 (1997): 834-43. PubMed.
    I'm using the product for the very purpose and benefits in the fact that specifically the 3,4-divanillyltetrahydrofuran lignan has the highest affinity for binding the SHBG. Not all lignans are equal, nor do all nettle root etxracts contain the same lignans.
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    Quote Originally Posted by AthleticXtrem View Post
    It would take a while and a lot of volume. I just don't see it being feasible for a company to have a $350 product that has 500mg a day of pure 3,4. No one would buy it, and no other companies would follow lead. Trust me it has been investigated heavily and is a very long process to create hence the expense.

    It's often a balance of innovation and what the market will bear. We research many compounds that need to be purified from an extract or synthesized and 70% of the time, the market would just not bear the price.

    However we are beginning testing after a successful synth of a pure testosterone mimitec that has never been seen before. It's been two years in the works and could be the biggest product we have ever come out. It will still be expensive but the market could bear it for this product.
    Ok so this all leaves me with a question. Although the studies show 3,4-divan has a high shbg affinity and considering that you state no products you tested had more than 5% in them, which of these two is more likely (just your opinion)

    1) that other ligands contribute significantly to the SHBG lowering effect as well
    2) the actual amount of 3,4 divan required to significantly drop SHBG is much lower than people thought

    Because there are a decent amount of peoples bloodworks (my own included) that showed that some of the major 3,4 containing products out there do lower SHBG significantly.
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    I am sure this must have been covered either in here or in the lengthy thread on BB but just to clarify because I don't remember the answer.

    How did so many companies go along with what they thought was a 95% extract when it was less than 5%?
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    Im subbed for more info on this! I still see alot of 95% extracts out there right now!!!!!!
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    Point to note:

    The NEW Activate Xtreme Ingredient profile now states: Divanil (Propietary Urtica Dioica Extract containing SHBG Binding and Aromatase Inhibiting Lignana Including 3,4-Divanillyltetrahydrofuran Secoisolariciresinol)

    Where as the ORIGINAL Activate Xtreme Ingredient profile stated: Divanil™ [95% 3,4-Divanillyltetrahydrofuran from Urtica Dioica]

    This suggests to me that they may have become aware and adjusted accordingly to comply with federal labeling requirements as AthleticXtrem stated:
    Quote Originally Posted by AthleticXtrem
    led AX to change its labels to identify the material as “a proprietary extract of the Urtica dioca plant” to comply with federal labeling regulations.
    Quote Originally Posted by EasyEJL
    1) that other ligands contribute significantly to the SHBG lowering effect as well
    2) the actual amount of 3,4 divan required to significantly drop SHBG is much lower than people thought
    I suspect the answer is both 1 & 2. I'll await AthleticXtrem reply.

    Lignans from the roots of Urtica dioica and their metabolites bind to human sex hormone binding globulin (SHBG).

    Schöttner M, Gansser D, Spiteller G.

    Lehrstuhl Organische Chemie I, Universität Bayreuth, Germany.
    Abstract

    Polar extracts of the stinging nettle (Urtica dioica L.) roots contain the ligans (+)-neoolivil, (-)-secoisolariciresinol, dehydrodiconiferyl alcohol, isolariciresinol, pinoresinol, and 3,4-divanillyltetrahydrofuran. These compounds were either isolated from Urtica roots, or obtained semisynthetically. Their affinity to human sex hormone binding globulin (SHBG) was tested in an in vitro assay. In addition, the main intestinal transformation products of plant lignans in humans, enterodiol and enterolactone, together with enterofuran were checked for their activity. All lignans except (-)-pinoresinol developed a binding affinity to SHBG in the in vitro assay. The affinity of (-)-3,4-divanillyltetrahydrofuran was outstandingly high. These findings are discussed with respect to potential beneficial effects of plant lignans on benign prostatic hyperplasia (BPH).

    PMID: 9434605 [PubMed - indexed for MEDLINE]
    http://www.ncbi.nlm.nih.gov/pubmed/9434605
    Interaction of lignans with human sex hormone binding globulin (SHBG).

    Schöttner M, Gansser D, Spiteller G.

    Lehrstuhl Organische Chemie I, Universität Bayreuth, Germany.
    Abstract

    Lignans bind to sex hormone-binding globulin (SHBG). The lignan with the highest binding affinity is (+/-)-3,4-divanillyltetrahydrofuran. In a double Stobbe condensation--without use of protecting groups--a wide variety of lignans with different substitution pattern in the aromatic and aliphatic part of the molecule was synthesized. These lignans were tested in a SHBG-binding assay which allowed to deduce the following relationship between structure and activity: 1) (+/-)-diastereoisomers are more active than meso compounds 2.) the 4-hydroxy-3-methoxy (guajacyl) substitution pattern in the aromatic part is most effective 3.) the activity increases with the decline in polarity of the aliphatic part of the molecule.

    PMID: 9463941 [PubMed - indexed for MEDLINE]http://www.ncbi.nlm.nih.gov/pubmed/9463941
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    Quote Originally Posted by bdcc View Post
    I am sure this must have been covered either in here or in the lengthy thread on BB but just to clarify because I don't remember the answer.

    How did so many companies go along with what they thought was a 95% extract when it was less than 5%?
    because everyone was getting such good results from it. and if one company says mine is 95%, are other company's going to say theirs is less than 5%?




    hey if it aint broke........
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    Additionally, really, how many companies actually test their actives for purity. It is costly and time consuming. I'm going to take the view that it was unintentional proliferation of misinformation on their label claims
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    Quote Originally Posted by Heat Miser View Post
    Additionally, really, how many companies actually test their actives for purity. It is costly and time consuming. I'm going to take the view that it was unintentional proliferation of misinformation on their label claims
    i accept also. there was no reason to say it was 95%, hell no one knew much about the extract when it 1st came out. if they would have said it was 5%, and everyone was getting good results who the hell would have cared what the percentage was....
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    Quote Originally Posted by EasyEJL View Post
    Ok so this all leaves me with a question. Although the studies show 3,4-divan has a high shbg affinity and considering that you state no products you tested had more than 5% in them, which of these two is more likely (just your opinion)

    1) that other ligands contribute significantly to the SHBG lowering effect as well
    2) the actual amount of 3,4 divan required to significantly drop SHBG is much lower than people thought

    Because there are a decent amount of peoples bloodworks (my own included) that showed that some of the major 3,4 containing products out there do lower SHBG significantly.
    Yes and the university study with Mass-FX also verified the major increase in free test so we know it is not placebo and is not duplicated with crude nettle extract. So for part of the testing we tried to have Chromadex identify the major components which just became to costly. So what we did find is that it is 100% nettle, has no synthetic properties, and is non-steroidal. So with that knowledge our guess is number one however it would take another 30k or so in spending to start to tap into the mystery. Honest answer with no spin.

    Does it work? Yes absolutely. What in the extract is doing the work? No one knows for sure.
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    Quote Originally Posted by thebigt View Post
    because everyone was getting such good results from it. and if one company says mine is 95%, are other company's going to say theirs is less than 5%?

    hey if it aint broke........
    Precisely my argument when this news first broke. If one were getting the results at 5% but were under the assumption that it was 95%, then that person was still seeing excellent results regardless of the number. Yes, the number does make a big difference, but if everyone was universally mislabeled, then one would assume that the problem was higher up the foodchain (ie suppliers).

    Quote Originally Posted by Heat Miser View Post
    Additionally, really, how many companies actually test their actives for purity. It is costly and time consuming. I'm going to take the view that it was unintentional proliferation of misinformation on their label claims
    You know of one of them. It's the same one that I do.

    Quote Originally Posted by thebigt View Post
    i accept also. there was no reason to say it was 95%, hell no one knew much about the extract when it 1st came out. if they would have said it was 5%, and everyone was getting good results who the hell would have cared what the percentage was....
    While I do not know the in's and out's of it all, from an outside observer's standpoint, I could see it feasible if one or two raw suppliers were labeling it as 95% and it was simply accepted by the supp companies who purchased those raws. Not until a pure sample was obtained and the myriad of products tested did this come to light. If I were an owner and I found out that I was handed something that was 90% off from what I was being sold, I would be slightly miffed to say the least. I think this is a prime example of the industry working together to get things tested properly and fixing label claims as they should be.

    And still, results is results. I've always reacted well to it. Hell, the original MassFX is why I got hooked on AX in the first place! To this day, that li'l 5% treats me well, so I'm not going to complain about it.
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    I think the consensus is that 95% may exist but it cannot be tested for, so it can't be claimed you have 95% if it cant be tested. That was the reason for the Divanex label change.

    That is just what I heard through the grapevine

    Not sure what the NOW stuff is...I think it is a totally different extract. But people do get noticeable results from the Divanex, so whatever % it is, it works . And I am sure the other companies are using a powder of the same quality
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    Quote Originally Posted by nattydisaster View Post
    I think the consensus is that 95% may exist but it cannot be tested for, so it can't be claimed you have 95% if it cant be tested. That was the reason for the Divanex label change.
    No it can be tested for. Chromadex has a pure reference sample. Until it was created no one questioned it. Anyone can test their extract against the standard as it is open to anyone via Chromadex. You simply have to call and ask to have your material/product tested against the reference named "Anseco".
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    Makes sense. Good info!
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