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Class of Natural Product: Perfumery (3,4)

Bisabolol is classified as a sesquiterpenoid, which are terpenoids consisting of three isoprene units and 15 carbon atoms. It is isolated from plants like chamomile and has the chemical formula C15H26O. Bisabolol has weak sweet and floral aroma, low density, and is insoluble in water but soluble in ethanol. Its main constituents are (-)-α-bisabolol, (-)-α-bisabolol oxides A, and (-)-α-bisabolol oxides B.

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53 views7 pages

Class of Natural Product: Perfumery (3,4)

Bisabolol is classified as a sesquiterpenoid, which are terpenoids consisting of three isoprene units and 15 carbon atoms. It is isolated from plants like chamomile and has the chemical formula C15H26O. Bisabolol has weak sweet and floral aroma, low density, and is insoluble in water but soluble in ethanol. Its main constituents are (-)-α-bisabolol, (-)-α-bisabolol oxides A, and (-)-α-bisabolol oxides B.

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Weixuan See
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Class of natural product

• Classified as terpenoids [1-3].


• Isolated from turpentine, a volatile liquid isolated from pine trees [3].
- which give plants and flowers their fragrance [3].
• Terpenoids are constituents of the essential oils of plants and flowers.
- Used as natural flavour additives for food, as fragrances in
perfumery [3,4].
• Built up from terpene building blocks [3].
- Each terpene consists of two paired isoprenes.
Classification of Terpenoids
• Terpenoids are the hydrocarbons of plant origin of the general formula
(C5H8)n [3].
• Bisabolol is classified under class ‘ Sesquiterpenoids’ based on the basis
of value of n or number of carbon atoms present in the structure [3,5].
Number of carbon Value of n Class
atoms
10 2 Monoterpenoids (C10H16)
15 3 Sesquiterpenoids (C15H24)
20 4 Diterpenoids (C20H32)
25 5 Sesterpenoids (C25H40)
30 6 Triterpenoids (C30H48)
40 8 Tetraterpenoids (C40H64)
>40 >8 Polyterpenoids (C5H8)n
Sesquiterpenes
• Sesquiterpene is a class of terpenes that consist of three isoprene
units [5].
• has molecular formula C15H24 [5].
• Like monoterpenes, sesquiterpenes may be acyclic or contain rings.
• Found naturally in plants and insects such as [5]
- Ginger
- Big Sagebrush
- Chamomile
- Artemisinin
Chemical and physical properties
• IUPAC Name: 6-methyl-2-(4-
methylcyclohex-3-en-1-yl)hept-5-en-2-ol
• Chemical formula: C15H26O
• Molar mass: 222.37 g/mol−1
• Weak sweet flora aroma
• Colourless liquid
• Low density (0.93 g cm−3) Figure 1. Structure of bisabolol [5,6]

• Boiling point (153oC at 12 Torr(mmHg))


• Lipophilic substance, with a propensity to
oxidise
• Insoluble in water, soluble in ethanol
Main constituents

(-)-α-bisabolol (-)-α-bisabolol oxides A (-)-α-bisabolol oxides B


Reference
• 1. Sesquiterpene [Internet]. En.wikipedia.org. 2018 [cited 10 November
2018]. Available from: https://en.wikipedia.org/wiki/Sesquiterpene
• 2. Terpenoid [Internet]. En.wikipedia.org. 2018 [cited 10 November 2018].
Available from: https://en.wikipedia.org/wiki/Terpenoid
• 3. Yadav N et al. Chemistry of Terpenoids [Internet].
Globalresearchonline.net. 2018 [cited 10 November 2018]. Available from:
http://globalresearchonline.net/journalcontents/v27-2/45.pdf
• 4. Saxena M. Phytochemistry of Medicinal Plants [Internet]. Researchgate.
2013 [cited 10 November 2018]. Available from:
https://www.researchgate.net/publication/284425734_Phytochemistry_of
_Medicinal_Plants
• 5. Bisabolol [Internet]. En.wikipedia.org. 2018 [cited 10 November
2018]. Available from: https://en.wikipedia.org/wiki/Bisabolol
• 6. Compositae-Associated Allergic Contact Dermatitis from Bisabolol
[Internet]. Ovidsp. 2011 [cited 11 November 2018].

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