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  1. #1

    Default Synthetic Tobacco Chemistry

    I came across some fascinating notes that offer insight into the chemistry behind Tobacco accords in perfumery, and would like to copy a shorted excerpt of that information here, which might serve as useful reference.


    Tobacco

    This is one of my favorite families. I have previously described its key chemicals, including Tabanone (megastigmatrienone) (Symrise), dihydotabanone, oxophorone, isophyoryl acetate, oxotheaspirane, 4-oxo-beta-ionone and others. Herein I will describe:
    …
    Megastigmadienone: This is a very secret and impressive fine floral-fruity scent with an extremely deep and natural tobacco note. …. Megastigmadienone has been found in Virginia tobacco and passion fruit … These combinations of Megastigmadienone with other chemicals like oxane, tropathiane, thioterpineol, (a finer product compared to the better known and lesser thiocineol), 3-thiohexenol, … are amazing and full of beauty. Megastigmadienone will have a good future in the development of our profession.

    Tetrascone -- 1-(1,2,3,4-tetrahydro-4,4-dimethyl-1-naphtalenyl)-propan-1-one: This is a not well known chemical, and is missing from most laboratories. Tetrascone is delicately floral tobacco, not very strong but long-lasting, and quite elegant. The chemical imparts the perfumery note that many perfumers try to get when blending tobacco-influenced fragrances.
    It blends very well with tobacco absolutes, and myrrh. The chemical also blends well with tabanone, but only if skillfully dosed so as not to obscure the charm of Tetrascone. The material is fantastic with beta-damasceneone, beta-damascene, all damascones, …and with oils such as Roman chamomile ...and hyssop. ...
    …

    Tobacco

    The tobacco family of chemicals that we have discussed previously include the products 3,3,5-trimethyl cyclohexanone (Isoforone), beta-damascene and 2,2,6-trimethylcyclo-hex-5-ene-1,4-dione (Oxoforone) are still considered novelties. I would like to add the names of a few others, among the many possibilities:

    3-Megastigmatrienone is a product of supreme importance both in the perfumery of the future and in the chemical composition of today's tobacco. It has indescribable tobacco scents, is fruity, radiant, powerful and brilliant. Its use may lead us to a new era in perfumery. I have no hesitation in placing this aromatic chemical among the elite of the chemical products that include Hedione, the ionones, the damascones, theaspirane, etc.

    It blends with woody notes such as Timberol, with fruity, radiant beta-damascenone, alpha- and beta-damascones, with chamomile, theaspirane-type tea and with all types of woody and herbal essential oils, with Ambrox, Rose Oxide, Nerol, and others so sensational that is well worth the perfumer's effort to let his imagination run free and fully accept its enormous potential. It is incredible that, as with Krishnanol, the synthetic products smell exactly the same as aromatic chemicals of natural origin such as Vetiveryl Acetate or Vetivrol. Excellent bases have been created with 3-megastigmatrienone such as those called Cienfuegos and Sumatra or Tobacco Leaf, other sensational blends are obtained by mixing this product with oxo-damascene, oxo-edulane and 4-oxo-beta-ionyl acetate.

    Oxophoyl has a penetrating, pungent and to some extent eucalyptus cool and with a very interesting backnote of seaweed, herbal, tobacco, smelling like a newly opened package of cigarettes. It is extraordinary in combination with Edulane, Tetrahydro edulane, Oxoforone, Oxo-damascene and 3-Megastrigmatrienone.

    Isophoryl acetate has a tremendously natural typical tobacco fragrance, with burnt and caramelized herbal backnotes, which blends perfectly with fruity and woody chemicals.

    3-Theaspirone or Oxo-Theaspirane has a fragrance similar to isophoryl acetate, but less dry, more woody-moist, camphoraceous, eucalyptus and deeply reminiscent of tobacco. It must also be said that all these products I am describing have been selected from among hundreds o others, and the mixtures among them are extraordinary.

    4-Oxo-beta-ionone is a crystallized product with an appearance rather similar to that of coumarine. It is much weaker than coumarin, but it has some of its effects, and when well applied it is full of novelty and enchantment. Its ability to be combined with powdery notes is sensational. It blends well with woody and balsamic vanilla notes and with cumin. Blends of 4-oxo-beta-ionone with 3-Megastigmatrienone, alpha-Damascone, Brahmanol, and Krishnanol are extraordinary because 4-oxo-beta-ionone powerfully fixes the effect of these aromatic chemicals.
    4-Oxo-beta-ionyl acetate has extraordinary and sensational tobacco, fruity fragrance, with important connotations of oxo-Edulane. …

    Perfumery: Techniques in Evolution, Arcadi Boix Camps, 2000

    Megastigmatrienone is also supposed to be reminiscent of Chardonnay wine.



    Tobacco
    A Review by John C. Leffingwell, Ph.D.

    This a part of our series on aroma materials produced by carotenoid degradation.
    As plants mature, or die, the chlorophyllic pigments rapidly decrease and virtually disappear (one of the normal catabolic changes during plant senescence). This is shown below for Burley tobacco after harvest, but is undoubtedly similar for other (green) plants. Many of the same carotenoid degradation products found in tobacco are also found in osmanthus, saffron, rose, boronia, quince & grapes.

    The graphs below show dramatically the transformation in pigments as plants die.
    [graph shows almost no chlorophyll left relative to initial amount after 20 days, barn cured burley tobacco]

    The yellow-orange carotenoid pigments of plants also decrease during the senescence or death phase of plants, but do not always decrease to the point of near extinction as do the chlorophyllic pigments. For example, using the same plant (tobacco) shown above...we see that the major carotenoids due not totally disappear. Much of the loss is due to enzymatic oxidative degradation. However, it should be noted that such oxidative degradation is also occurring during the life of the plant (not just in the death phase). In fact, photo-oxidation of carotenoids in living plants (i.e. flowers) is often responsible for its odor.
    [graph shows carotenoid pigments down to a third of initial starting amounts after 20 days]

    Many important carotenoid aroma constituents are formed during this decrease after harvesting and during the curing.
    While no one or two components comprise the aroma of cured tobacco, the following constituents are reported as being important:
    beta-Damascenone, Megastigmatrienones (4-isomers)

    http://www.leffingwell.com/tob.htm


    Aroma Properties of Selected Tobacco Carotenoid Derivatives

    beta-Damascenone - Fruity, floral with apple, plum-raisen, tea, rose, tobacco note
    Oxo-Edulan - Oriental Tobacco like
    Theaspirone - Tea like
    4-Oxo-beta-ionone - Sweet rich like Virginia tobacco
    Safanal - Saffron, green, sweet, hay-like
    beta-Cyclocitral - Green, grassy hay like odor

    http://www.leffingwell.com/tob2.htm

  2. #2

    Default Re: Synthetic Tobacco Chemistry

    Interesting, it looks like many of the active fragrance chemicals in Osmanthus are the same ones in Tobacco.

    Osmanthus fragrans (Oleaceae)
    Osmanthus, also called 'sweet olive', is a bush of the olive family from the Far East. Its plenty of small flowers give off an overwhelmingly sweet fragrance with a fruity nuance, resembling that of ripe apricots. In China they are used for perfuming tea. Moreover, a so-called osmanthus absolute is obtained by extraction of the flowers. It is a valuable ingredient in the art of perfumery. Its major constituents are variations on the structure of ionone: beta-ionone (10 %) and beta-damascenone, theaspirane and theaspirone, megastigmadienone and -trienone, etc. Furthermore,
    (+)-gamma-decalactone (4 %) is a character impact compound.

    http://www.bojensen.net/EssentialOil...ialOils22A.htm


    I wouldn't be surprised if there are some parallels with Cognac as well.

  3. #3

    Default Re: Synthetic Tobacco Chemistry

    Both Solanone and Pomarose may be useful here.

    Pomarose is a good synthetic replacement for damascenone in fragrances.

    Solanone is supposed to have a slight sweetness to it, reminiscent of tobacco, a bit fruity, and aquatic/melon.
    Solanone is actually one of the natural constituents in the headspace of tobacco, but is often synthetically added to cigarette tobacco to improve aroma.

    The chemical structure of Solanone is CH3COCH2CH2C(CH(CH3)2)CH=CHC(CH3)=CH2
    Pomarose is CH3CH=CHCOC(CH3)=C(CH3)CH(CH3)2

    Both Solanone and Pomarose are ketones with similar fragrance-chemical-type structures.

  4. #4

    Default Re: Synthetic Tobacco Chemistry

    Parker, I am fascinated by the carotenoid degredation by-products, they are all the things you need for rose in trace amounts - beta ionine, damascones and damascenones.
    The degradation can be done with simple soil microbes on grapes, carrots, beets, etc. (My first attempt was not something I wanted to filter)
    There is damascenone produced as a result of distilling beer and wine as well. I think microbreweries have to add this as they need to get the sharpness, and are not as equipped to have hops as fresh as the major companies.
    I also read that geraniol is essential to getting non-scented flowers to bloom, some rose varieties are missing geraniol and do not give up scent.
    It leads you to wonder:
    * are all flowers that do not give aroma just 'missing' geraniol, like we could put it in there and they will give it up?
    * Why then, with so many articles about this carotenoid - geraniol combo, do white flowers have the strongest scent?
    I will definitely look into pomarose - I used some rosehip oil, that has very little scent, in geraniol - and it changes toward rose almost daily.

  5. #5

    Default Re: Synthetic Tobacco Chemistry

    Quote Originally Posted by Thea in Fl View Post
    are all flowers that do not give aroma just 'missing' geraniol, like we could put it in there and they will give it up?
    I do not think so, geraniol is only one of many fragrance compounds. Anyone who has smelled rose geranium probably has a good idea what geraniol smells like. It smells characteristically like rose, but not necessarily the most desirable fragrance aspect.
    Also realize there's a difference between the smell of ketones/aldehydes and alcohols. Alcohols smell sharper. Think about the smell of phenethyl alcohol, it smells rose-like, but to my nose more like the aspect of a wilted rose or potpourri.
    Even the aldehyde version of geraniol, which we would expect to smell more sweetly pleasant, is citral, is the smell of lemongrass.

    You're also assuming a causative relationship from correlation, probably wrongly.
    Rose varieties that do not put out scent would not put out geraniol. There's a whole host of different fragrance compounds that come from the same biologic pathway, and geraniol is only one of them. So it's only an indicator, most likely.

    Quote Originally Posted by Thea in Fl View Post
    I will definitely look into pomarose
    Even though pomarose does not really have the same chemical structure as damascenone, apparently the molecule does have the same (or very similar) functional shape and can mimic the odor sensation.

  6. #6

    Default Re: Synthetic Tobacco Chemistry

    Well, back to tobacco, I think that black tea and basil have tobacco character.

  7. #7

    Default Re: Synthetic Tobacco Chemistry

    Quote Originally Posted by Thea in Fl View Post
    basil have tobacco character.
    Just an idea I had, I wonder if tomato leaf would have any tobacco character, especially if cured to bring out the aroma.
    Tobacco and tomato are both in the same distant family.

  8. #8

    Default Re: Synthetic Tobacco Chemistry

    Symroxane imparts tobacco/damascenone-like effects.
    (described as woody, vetiver, dried fruit, tobacco)

  9. #9

    Default Re: Synthetic Tobacco Chemistry

    Tabanone - warm-tobacco, sweet, fruity-plum, acorn, dry. very powerful
    Arcadi Boix Camps, writes in 1985 about this material with great enthusiasm describing it as "a product of supreme importance both in the perfumery of the future and the chemical composition of todays tobacco. It has indescribable tobacco scents, is fruity, radiant, powerful and brilliant. Its use may lead us to a new era in perfumery. I have no hesitation in placing this aromaic chemical among the elite of the chemical products that include Hedione, the irones, the Damascones, and theaspirane"

    (chemically it's related to megastigmadienone)


    Also, just to point out, Safranal seems quite similar to benzaldehyde in structure, the only difference is a methyl group in the 2-position, and another two methyl groups on the 6-position. I wonder if this is the compound that lends tobacco its cherry-like note? The fragrance literature doesn't list it as cherry though.

  10. #10

    Default Re: Synthetic Tobacco Chemistry

    Thought I would add Trimofix O to the equation, I find it very beautiful:
    To me it's a dry tobacco note with ambergris and cedramber qualities, very strong.

    TRIMOFIX "O" TT
    Amber Decatriene, Trimofix O. Fixamber Ambergris, woody, cedar, dry tobacco, musk. use up to 5%
    Powerful, diffusive, amber, woody note with vetiver and smoky, tobacco

    Odor Strength: Medium

    Odor Type: Wood

    Longevity: 284 Hours

    Note: middle

    Use Up To: 5%

    In Fragrance Concentration.

    Flash Point: 201.00 °F. TCC ( 93.89 °C. )

    SDS

    CAS # Mixture

  11. #11

    Default Re: Synthetic Tobacco Chemistry

    Quote Originally Posted by SharpLess View Post
    Thought I would add Trimofix O to the equation, I find it very beautiful:
    Interesting. Also known as amber decatriene or methyl trimethylcyclododecatrienyl ketone, cyclisone, and alternatively marketed as Fixamber. It's said to only have tobacco nuances though.

    (chemical structure is a 12-member carbon ring, with an acetyl group in the 1-position, methyl groups in the 4, 8, and 12-positions, and double bonds in the 4-5, 8-9, 11-12 positions. It's a ketone. molecular formula C17H26O. To me it bears structural resemblance to incensole acetate, the compound primarily responsible for the smell of frankincense, although of course not really the same)

    Just looking at the molecular structure I can tell that it would smell like tobacco.

    ambergris, woody, cedar, dry tobacco, musk
    Perfumer's Apprentice: Powerful and diffusive, amber and woody note with slight musk and tobacco undertones.


    Also to add, Orspirane (related to theaspirane) might be useful for recreating fresh green tobacco accords.




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