Nerolidol

*trans*-Nerolidol (top) and *cis*-Nerolidol (bottom)
Names


IUPAC name 3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol
Other names Peruviol
Identifiers
CAS Number	7212-44-4 (unspecified) 3790-78-1 (6-Z) 40716-66-3 (6-E)
3D model (JSmol)	(unspecified): Interactive image (cis): Interactive image (trans): Interactive image
ChEBI	CHEBI:7524 (unspecified) CHEBI:173119 (cis) CHEBI:141283 (trans)
ChemSpider	8549 (unspecified) 4478283 (cis) 4447568 (trans)
ECHA InfoCard	100.027.816
PubChem CID	8888 (unspecified) 5320128 (cis) 5284507 (trans)
UNII	QR6IP857S6 (unspecified) 81K23DEF7B (cis) FG5V0N8P2H (trans)
CompTox Dashboard (EPA)	DTXSID3022247
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,1,7-8,10,12H2,2-5H3 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
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 (n_D)	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 by, the addition of vinyl Grignard reagent. It is used as a source of farnesol, vitamin E, and vitamin K1.

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.

References※

^ Merck Index, 11th Edition, 6388.
^ 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.
^ 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.
^ Sell, "Charles S." (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN 0471238961.
^ Kaiser, Roman (1993). The Scent of Orchids. Elsevier. pp. 58, 199–200. ISBN 978-0-444-89841-8.

Categories:

XIV

Synthesis and occurrence※

See also※

References※