Nerolidol

*trans*-Nerolidol (top) and *cis*-Nerolidol (bottom)^[1]
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/cm3
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 [77 °F], 100 kPa). verify (what is ?) Infobox references

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] Nerolidyl derivatives include nerolidyl diphosphate^[3] and the fragrance nerolidyl acetate.^[4]

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.^[4]

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.^[4] 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.^[5]

References

^ ^a ^b 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.
^ ^a ^b ^c 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.

[Merck-1] Merck Index, 11th Edition, 6388.

[:0-2] 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.

[KO-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.

[1]

[2]

[3]

[4]

[5]

Nerolidol

Synthesis and occurrence

See also

References

Pfad - The Proxy pFad of © 2024 Garber Painting. All rights reserved.