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 (cis) ; 40716-66-3 (trans) ;
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
	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 found in the essential oils of many types of plants and flowers.^[1]^[2] There are two isomers of nerolidol, cis and trans, which differ in the geometry about the central double bond. Nerolidol is present in neroli, ginger, jasmine, lavender, tea tree, Cannabis sativa, and lemon grass, and is a dominant scent compound in Brassavola nodosa.^[3] The aroma of nerolidol is woody and reminiscent of fresh bark. It is used as a flavoring agent and in perfumery and is used in non-cosmetic products such as detergents and cleansers.^[4] It is currently^[when?] under testing as a skin penetration enhancer for the transdermal delivery of therapeutic drugs.^[5] Additionally, it is known for various biological activities include antioxidant, anti fungal, anticancer, and antimicrobial activity.^[4] It is one of several organic volatiles produced by the Arabidopsis lyrata ssp. petraea flower in response to insect feeding.^[6] Because of its hydrophobic nature, nerolidol is easily permeable across the plasma membrane and can interact with intracellular proteins.^[4] However it has a high cytotoxic potential and can disrupt the membrane.^[4]

Nerolidyl compounds involve joining nerolidol at the oxygen atom to other groups, and include Nerolidyl diphosphate.^[7]

References

^ ^a ^b Merck Index, 11th Edition, 6388.
^ Miguel, M.G.; Dandlen, S.; Figueiredo, A.C.; Barroso, J.G.; Pedro, L.G.; Duarte, A.; Faisca, J. (2008). "ESSENTIAL OILS OF FLOWERS OF CITRUS SINENSIS AND CITRUS CLEMENTINA CULTIVATED IN ALGARVE, PORTUGAL". Acta Horticulturae (773): 89–94. doi:10.17660/ActaHortic.2008.773.12. ISSN 0567-7572.
^ Kaiser, Roman (1993). The Scent of Orchids. Elsevier. pp. 58, 199–200. ISBN 978-0-444-89841-8.
^ ^a ^b ^c ^d 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.
^ K. Moser et al. European Journal of Pharmaceutics and Biopharmaceutics 52 (2001) 103-112 doi:10.1016/S0939-6411(01)00166-7
^ Abel, Christian; Clauss, Maria; Schaub, Andrea; Gershenzon, Jonathan; Tholl, Dorothea (2009). "Floral and insect-induced volatile formation in Arabidopsis lyrata ssp. petraea, a perennial, outcrossing relative of A. thaliana". Planta. 230 (1): 1–11. doi:10.1007/s00425-009-0921-7. PMC 2687518. PMID 19322583.
^ 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.

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

[2] Miguel, M.G.; Dandlen, S.; Figueiredo, A.C.; Barroso, J.G.; Pedro, L.G.; Duarte, A.; Faisca, J. (2008). "ESSENTIAL OILS OF FLOWERS OF CITRUS SINENSIS AND CITRUS CLEMENTINA CULTIVATED IN ALGARVE, PORTUGAL". Acta Horticulturae (773): 89–94. doi:10.17660/ActaHortic.2008.773.12. ISSN 0567-7572.

[3] Kaiser, Roman (1993). The Scent of Orchids. Elsevier. pp. 58, 199–200. ISBN 978-0-444-89841-8.

[:0-4] 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.

[5] K. Moser et al. European Journal of Pharmaceutics and Biopharmaceutics 52 (2001) 103-112 doi:10.1016/S0939-6411(01)00166-7

[6] Abel, Christian; Clauss, Maria; Schaub, Andrea; Gershenzon, Jonathan; Tholl, Dorothea (2009). "Floral and insect-induced volatile formation in Arabidopsis lyrata ssp. petraea, a perennial, outcrossing relative of A. thaliana". Planta. 230 (1): 1–11. doi:10.1007/s00425-009-0921-7. PMC 2687518. PMID 19322583.

[7] 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.

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See also

References