Nerolidol

Structural formula
trans -Nerolidol (left) and cis -Nerolidol (right) - in each case racemates
General
Surname	Nerolidol
other names	3,7,11-trimethyl-1,6,10-dodecatrien-3-ol
Molecular formula	C 15 H 26 O
Brief description	colorless to light yellow liquid
External identifiers / databases
CAS number 7212-44-4 (mixture of isomers) EC number 230-597-5 ECHA InfoCard 100,027,816 PubChem 8888 Wikidata Q72494054
properties
Molar mass	222.37 g mol −1
Physical state	liquid
density	0.88 g cm −3
boiling point	145–146 ° C (16 h Pa )
solubility	bad in water
safety instructions
GHS labeling of hazardous substances Mixture of isomers Caution H and P phrases H: 317-319-410 P: ?
Toxicological data	> 5000 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Nerolidol is one of the acyclic sesquiterpenes or rather one of the sesquiterpene alcohols. It is the main ingredient in Cabreuva oil . Nerolidol is an isomer of farnesol . Both alcohols contain three double bonds, whereby nerolidol differs from farnesol in the position of a double bond and the OH group.

Occurrence

Orange blossom and orange - the essential oil neroli, which contains nerolidol, is extracted from the blossoms.

Nerolidol is found in neroli , ginger , jasmine , lavender , tea tree , cannabis and lemongrass and is a component of many essential oils, e.g. B. Peru balsam oil and Cabreuva oil. It is used as a flavoring and fragrance .

biosynthesis

(3 S , 6 E ) -Nerolidol occurs naturally as an intermediate in the biosynthesis of 4,8-dimethyl-1,3 ( E ), 7-nonatriene. It is formed by the enzyme nerolidol synthase ( EC  4.2.3.48 ) from (2 E , 6 E ) - farnesyl pyrophosphate by splitting off pyrophosphate (PP _i ).

Isomers

Nerolidol has a center of chirality and, if not specified in more detail, is present as a mixture of a total of four cis / trans and ( R ) / ( S ) isomers.

Isomers of nerolidol
Surname	( R ) - cis - Nerolidol	( S ) - cis - Nerolidol	( R ) - trans - Nerolidol	( S ) - trans - Nerolidol
Structural formula
other names	(3 R , 6 Z ) - (-) - Nerolidol	(3 S , 6 Z ) - (+) - Nerolidol	(3 R , 6 E ) - (+) - Nerolidol	(3 S , 6 E ) - (-) - Nerolidol
CAS number	132958-73-7	142-50-7	77551-75-8	1119-38-6
	3790-78-1 [( Z ) -isomers]		40716-66-3 [( E ) -isomers]
	7212-44-4 (mixture of isomers)
PubChem	12227246	5356544	11241545	5281525
	8888 (mixture of isomers)
odor	intensely flowery, sweet and fresh	pleasant, woody, warm and musty	woody, green and bark	slightly sweet, mild and flowery
GHS labeling	no GHS pictograms		Caution
H and P phrases	no H-phrases		315-319-335
	no P-phrases		261-305 + 351 + 338

Individual evidence

1. ↑ ^{a b c} Entry on nerolidol. In: Römpp Online . Georg Thieme Verlag, accessed on June 22, 2014.
2. ↑ ^{a b} data sheet cis-nerolidol (PDF) from Carl Roth , accessed on February 18, 2018.
3. ↑ Entry on nerolidol, mixture of isomers in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
4. ^ Entry on nerolidol in the ChemIDplus database of the United States National Library of Medicine (NLM) .
5. ↑ The European Bioinformatics Institute: EC 4.2.3.48, (3S, 6E) -nerolidol synthase .
6. ↑ Wolfgang Legrum: Fragrances, between stink and fragrance , Vieweg + Teubner Verlag (2011) pp. 34–35, ISBN 978-3-8348-1245-2 .
7. ^ Entry on trans-Nerolidol in the GESTIS substance database of the IFA , accessed on February 8, 2018(JavaScript required) .