Nerolidol

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]

trans-Nerolidol (top) and cis-Nerolidol (bottom)^[1]

trans-Nerolidol
cis-Nerolidol
Names
IUPAC name 3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol
Other names Peruviol
Identifiers
CAS Number	7212-44-4 (unspecified) Y 3790-78-1 (6-Z) Y 40716-66-3 (6-E) Y
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) N 4478283 (cis) N 4447568 (trans) N
ECHA InfoCard	100.027.816
PubChem CID	8888 (unspecified) 5320128 (cis) 5284507 (trans)
UNII	QR6IP857S6 (unspecified) Y 81K23DEF7B (cis) Y FG5V0N8P2H (trans) Y
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). N verify (what is YN ?) Infobox references

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]

See also

• Linalool
• Farnesol