Bisabolol

Soh Khai Xin 00000026457

Lim Jun Ann 00000026206
See We Xuan 00000023271
 (+)-4-epi-alpha-bisabolol

bisabolol, (+)-isomer
Synonms [1]
bisabolol, (-)-isomer

levomenol
Isomer [2]
 Natural source of bisabolol [2]

• German chamomile (Matricaria chamomilla)

• sage (Salvia runcinata and certain chemotypes of the closely related
S. stenophylla)
• Vanillosmopsis sp. (e.g. V. pohlii, V. arborea)
• Myoporum grassifolium (richest source [3])
• wood of Candeia (Eremanthus erythropappus)
• Plinia cerrocampanensis (found in 2010 [4] ）
German chamomile sage (Salvia
(Matricaria chamomilla) runcinate)
Myoporum wood of Candeia
grassifolium (Eremanthus
erythropappus)
• Plinia
cerrocampanensis
Type of natural products
monocyclic sesquiterpene alcohol 【 2 】
 Class of natural product

• Classified as terpenoids [5-7].

• Isolated from turpentine, a volatile liquid isolated from pine trees [7].
- which give plants and flowers their fragrance [7].
• Terpenoids are constituents of the essential oils of plants and flowers.
- Used as natural flavour additives for food, as fragrances in
perfumery [7,8].
• Built up from terpene building blocks [7].
- Each terpene consists of two paired isoprenes.
 Classification of Terpenoids
• Terpenoids are the hydrocarbons of plant origin of the general formula
(C5H8)n [7].
• Bisabolol is classified under class ‘ Sesquiterpenoids’ based on the basis
of value of n or number of carbon atoms present in the structure [7,9].
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

[9].
• has molecular formula C15H24 [9].
• Like monoterpenes, sesquiterpenes may be acyclic or contain rings.
• Found naturally in plants and insects such as [9]
- 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
Figure 1. Structure of bisabolol [5,6]
• Low density (0.93 g cm−3)
• 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

 Historical Uses of Bisabolol

• Anti-infective
• -bisabolol tested active against Gram-positive bacteria, fungi and
Candida albicans [9]
• Anti-plasmodial
• German chamomile oil can treat dizziness, neuralgia, muscle
cramping, headache, malaria and fever [10]
• Salvia runcinata tested active against the chloroquine-resistant strain
FCR-3 [10]
 Historical Uses of Bisabolol
• Anti-oxidant and anti-inflammatory activity
• Can treat several degenerative diseases such as brain dysfunction,
cancer, heart disease and immune system decline [11]

• Depigmentation effect on the skin [12]

 Benefits of Bisabolol in Skincare
Products
• Tames inflammation
• Moisturizes deeply
• Stimulates healing
• Kills germs
• Provide a natural scent without chemicals
• Helps fade/soften fine lines and wrinkles
• Fades hyperpigmentation [13]
 Benefits of Chamomile Tea

• Reducing menstrual pain • Cancer treatment and prevention

• Treating diabetes and lowering • Helping with sleep and relaxation

blood sugar (sedative)

• Slowing/preventing osteoporosis • Treating cold symptoms

• Reducing inflammation • Treating mild skin conditions[14]

 Reference
1. Bisabolol [Internet]. Pubchem.ncbi.nlm.nih.gov. 2018 [cited 10 November 2018]. Available from:
https://pubchem.ncbi.nlm.nih.gov/compound/10586#section=NSC-Number
2. Kamatou GPP, Viljoen AM. A Review of the Application and Pharmacological Properties of alpha]-
Bisabolol and alpha]-Bisabolol-Rich Oils. JAOCS, Journal of the American Oil Chemists' Society 2010
01;87(1):1-7.
3. Kirk R, Othmer D, Seidel A. Kirk-Othmer chemical technology of cosmetics. Hoboken (N.J.): Wiley; 2013.
4. Vila R, Santana A, Pérez-Rosés R, Valderrama A, Castelli M, Mendonca S et al. Composition and biological
activity of the essential oil from leaves of Plinia cerrocampanensis, a new source of α-bisabolol. Bioresource
Technology [Internet]. 2010 [cited 10 November 2018];101(7):2510-2514. Available from:
https://www.sciencedirect.com/science/article/pii/S0960852409015259
5. Sesquiterpene [Internet]. En.wikipedia.org. 2018 [cited 10 November 2018]. Available from:
https://en.wikipedia.org/wiki/Sesquiterpene
6. Terpenoid [Internet]. En.wikipedia.org. 2018 [cited 10 November 2018]. Available from:
https://en.wikipedia.org/wiki/Terpenoid
7. 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
8. Saxena M. Phytochemistry of Medicinal Plants [Internet]. Researchgate. 2013 [cited 10 November 2018].
9. Duke JA, Bogenschutz-Godwin MJ, DuCellier J, Duke P-AK (2002) Handbook of medicinal herbs,
2nd edn. CRC Press, Boca Raton
10. Kamatou GPP, Viljoen AM, Lourens ACU, Bas¸er KHC, Demirci B, Lindsey KL, Van Staden J,
Steenkamp P (2005) The in vitro pharmacological activities and a chemical investigation of three South
African Salvia species. J Ethnopharmacol 102:382–390
11. Aruoma OI (1998) Free radicals, oxidative stress and anti-oxidants in human health and disease. J
Am Oil Chem Soc 75:199–212
12. Kim S, Lee J, Jung E, Huh S, Park J-O, Lee J-W, Byun SY, Park D (2008) Mecahnisms of
depigmentation by a-bisabolol. J Dermatol Sci 52:219–222
13. 7 Ways Bisabolol Turns Back the Clock On Your Skin [Internet]. CV Skinlabs. 2018 [cited 11
November 2018]. Available from: https://cvskinlabs.com/7-ways-bisabolol-turns-back-the-clock-on-
your-skin/
14. Debra Sullivan C. 8 benefits of chamomile tea [Internet]. Medical News Today. 2018 [cited 11
November 2018]. Available from: https://www.medicalnewstoday.com/articles/320031.php