Nerolidol

Chemical compound From Wikipedia, the free encyclopedia

Nerolidol, also known as peruviol and penetrol, is a naturally occurring sesquiterpene alcohol. A colorless liquid, it is found in the essential oils of many types of plants and flowers.[1] There are four isomers of nerolidol', which differ in the geometry about the central double bond and configuration of the hydroxyl-bearing carbon, but most applications use such a mixture. The aroma of nerolidol is woody and reminiscent of fresh bark. It is used as a flavoring agent and in perfumery as well as in non-cosmetic products such as detergents and cleansers.[2] It has pronounced pharmacological properties: antimicrobial, antiparasitic, anti-inflammatory[3]. Nerolidyl derivatives include nerolidyl diphosphate[4] and the fragrance nerolidyl acetate.[5]

Quick facts Names, Identifiers ...
trans-Nerolidol (top) and cis-Nerolidol (bottom)[1]
trans-Nerolidol
trans-Nerolidol
cis-Nerolidol
cis-Nerolidol
Names
IUPAC name
3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol
Other names
Peruviol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.027.816 Edit this at Wikidata
UNII
  • (unspecified): InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3
    Key: FQTLCLSUCSAZDY-UHFFFAOYSA-N
  • (cis): InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/b14-11-
    Key: FQTLCLSUCSAZDY-KAMYIIQDSA-N
  • (trans): InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/b14-11+
    Key: FQTLCLSUCSAZDY-SDNWHVSQSA-N
  • (unspecified): OC(\C=C)(CCC=C(CC/C=C(\C)C)C)C
  • (cis): OC(\C=C)(CC\C=C(/CC/C=C(\C)C)C)C
  • (trans): CC(=CCC/C(=C/CCC(C)(C=C)O)/C)C
Properties
C15H26O
Molar mass 222.37 g/mol
Density 0.872 g/cm3
Boiling point 122 °C (252 °F; 395 K) at 3 mmHg
1.4898
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis and occurrence

Nerolidol is produced commercially from geranylacetone, e.g., by the addition of vinyl Grignard reagent. It is used as a source of farnesol, vitamin E, and vitamin K1.[5]

Conversion of geranylacetone to nerolidol, which can be isomerized to farnesol.

Significant sources of natural nerolidol is Cabreuva oil and the oil of Dalbergia parviflora.[5] It is also present in neroli, ginger, jasmine, lavender, tea tree, Cannabis sativa, and lemon grass, and is a dominant scent compound in Brassavola nodosa.[6]

See also

References

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