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268909

Sigma-Aldrich

cis-3,7-Dimethyl-2,6-octadien-1-ol

97%

Synonym(s):

Nerol

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About This Item

Linear Formula:
(CH3)2C=CHCH2CH2C(CH3)=CHCH2OH
CAS Number:
106-25-2
Molecular Weight:
154.25
Beilstein:
1722455
EC Number:
203-378-7
MDL number:
MFCD00063204
UNSPSC Code:
12352100
PubChem Substance ID:
24856300
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.474 (lit.)

bp

103-105 °C/9 mmHg (lit.)

solubility

absolute ethanol: soluble(lit.)

density

0.876 g/mL at 25 °C (lit.)

SMILES string

C\C(C)=C\CC\C(C)=C/CO

InChI

1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7-

InChI key

GLZPCOQZEFWAFX-YFHOEESVSA-N

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General description

The antifungal efficacy of nerol (cis-3,7-Dimethyl-2,6-octadien-1-ol), against Aspergillus flavus, was studied.

Application

cis-3,7-Dimethyl-2,6-octadien-1-ol was used in the highly convergent and stereocontrolled synthesis of epothilone D.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H317,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1B

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

226.0 °F - closed cup

Flash Point(C)

107.78 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Jun Tian et al.
TheScientificWorldJournal, 2013, 230795-230795 (2014-01-24)
The antifungal efficacy of nerol (NEL) has been proved against Aspergillus flavus by using in vitro and in vivo tests. The mycelial growth of A. flavus was completely inhibited at concentrations of 0.8 μ L/mL and 0.1 μ L/mL NEL
Ludger A Wessjohann et al.
The Journal of organic chemistry, 78(21), 10588-10595 (2013-10-02)
A highly convergent and stereocontrolled synthesis of epothilone D (4) is reported. Key features are a cheap and Z-selective synthesis of the northern half based on nerol and acetoacetate and chromium(II)-mediated Reformatsky reactions as a powerful tool for chemoselective asymmetric
Pankaj K Sharma et al.
Plant science : an international journal of experimental plant biology, 203-204, 63-73 (2013-02-19)
Plants synthesize volatile alcohol esters on environmental insult or as metabolic induction during flower/fruit development. However, essential oil plants constitutively produce them as the oil constituents. Their synthesis is catalyzed by BAHD family enzymes called alcohol acyltransferases (AATs). However, no
Bertrand Fouks et al.
The Journal of experimental biology, 216(Pt 2), 285-291 (2012-10-06)
Foraging is a result of innate and acquired mechanisms, and is optimized in order to increase fitness. During foraging, an animal faces many threats, such as predation and infection. The uptake of parasites and diseases while foraging is common and
Yukihiro Yamamoto et al.
Bioorganic & medicinal chemistry letters, 18(14), 4044-4046 (2008-06-17)
In order to prepare functional phospholipids in the medical and pharmaceutical fields, perillyl alcohol, myrtenol, and nerol were transphosphatidylated via phospholipase D in an aqueous system. The yields of phosphatidyl-perillyl alcohol, -myrtenol, and -nerol were 79 mol %, 87 mol
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