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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.

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