Open main menu

Wikipedia β

Nerolidol, also known as peruviol, is a naturally occurring sesquiterpene found in the essential oils of many types of plants and flowers.[1] There are two isomers of nerolidol, cis and trans, which differ in the geometry about the central double bond. Nerolidol is present in neroli, ginger, jasmine, lavender, tea tree, Cannabis sativa, and lemon grass, and is a dominant scent compound in Brassavola nodosa.[2] The aroma of nerolidol is woody and reminiscent of fresh bark. It is used as a flavoring agent and in perfumery. It is also used in non-cosmetic products such as detergents and cleansers.[3] It is also currently under testing as a skin penetration enhancer for the transdermal delivery of therapeutic drugs.[4] Additionally, it is known for various biological activities include antioxidant, anti fungal, anticancer, and antimicrobial activity.[3] It is one of several organic volatiles produced by the A. lyrata ssp. petraea flower in response to insect feeding.[5] Because of its hydrophobic nature, nerolidol is easily permeable across the plasma membrane and can interact with intracellular proteins.[3] However it has a high cytotoxic potential and can disrupt the membrane.[3]

trans-Nerolidol (top) and cis-Nerolidol (bottom)[1]
trans-Nerolidol
cis-Nerolidol
Names
IUPAC name
3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol
Other names
Peruviol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.027.816
Properties
C15H26O
Molar mass 222.37 g/mol
Density 0.872 g/cm3
Boiling point 122 °C (252 °F; 395 K) at 3 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

See alsoEdit

ReferencesEdit

  1. ^ a b Merck Index, 11th Edition, 6388.
  2. ^ Kaiser, Roman (1993). The Scent of Orchids. Elsevier. pp. 58, 199–200. ISBN 0-444-89841-7. 
  3. ^ a b c d Chan, Weng-Keong; Tan, Loh Teng-Hern; Chan, Kok-Gan; Lee, Learn-Han; Goh, Bey-Hing (2016-04-28). "Nerolidol: A Sesquiterpene Alcohol with Multi-Faceted Pharmacological and Biological Activities". Molecules. 21 (5): 529. doi:10.3390/molecules21050529. 
  4. ^ K. Moser et al. European Journal of Pharmaceutics and Biopharmaceutics 52 (2001) 103-112 doi:10.1016/S0939-6411(01)00166-7
  5. ^ Abel, Christian; Clauss, Maria; Schaub, Andrea; Gershenzon, Jonathan; Tholl, Dorothea. "Floral and insect-induced volatile formation in Arabidopsis lyrata ssp. petraea, a perennial, outcrossing relative of A. thaliana". Planta. 230 (1): 1–11. doi:10.1007/s00425-009-0921-7.