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Nerolidol

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trans-Nerolidol (top) and cis-Nerolidol (bottom)
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
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.027.816 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • (unspecified): InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3Key: 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
SMILES
  • (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
Chemical formula C15H26O
Molar mass 222.37 g/mol
Density 0.872 g/cm
Boiling point 122 °C (252 °F; 395 K) at 3 mmHg
Refractive index (nD) 1.4898
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. 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. Nerolidyl derivatives include nerolidyl diphosphate and the fragrance nerolidyl acetate.

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.

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. 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.

See also

References

  1. ^ Merck Index, 11th Edition, 6388.
  2. 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. PMC 6272852. PMID 27136520.
  3. Benedict, C. R. (1 April 2001). "The Cyclization of Farnesyl Diphosphate and Nerolidyl Diphosphate by a Purified Recombinant delta-Cadinene Synthase". Plant Physiology. 125 (4): 1754–1765. doi:10.1104/pp.125.4.1754. PMC 88832. PMID 11299356.[REDACTED]
  4. ^ Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
  5. Kaiser, Roman (1993). The Scent of Orchids. Elsevier. pp. 58, 199–200. ISBN 978-0-444-89841-8.
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