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Nerolidol

From Wikipedia, the free encyclopedia
trans-Nerolidol(top) andcis-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 InfoCard100.027.816Edit 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 mass222.37 g/mol
Density0.872 g/cm3
Boiling point122 °C (252 °F; 395 K) at 3 mmHg
1.4898
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

Nerolidol, also known asperuviol andpenetrol, is a naturally occurringsesquiterpene alcohol. A colorless liquid, it is found in theessential oils of many types of plants and flowers.[1] There are fourisomers 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]Nerolidyl derivatives includenerolidyl diphosphate[3] and the fragrance nerolidyl acetate.[4]

Synthesis and occurrence

[edit]

Nerolidol is produced commercially fromgeranylacetone, e.g., by the addition ofvinylGrignard reagent. It is used as a source offarnesol,vitamin E, andvitamin K1.[4]

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

Significant sources of natural nerolidol isCabreuva oil and the oil ofDalbergia parviflora.[4] It is also present inneroli,ginger,jasmine,lavender,tea tree,Cannabis sativa, andlemon grass, and is a dominant scent compound inBrassavola nodosa.[5]

See also

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References

[edit]
  1. ^abMerck 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.Open access icon
  4. ^abcSell, 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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