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268909

Sigma-Aldrich

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

97%

Sinónimos:

Nerol

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About This Item

Fórmula lineal:
(CH3)2C=CHCH2CH2C(CH3)=CHCH2OH
Número de CAS:
106-25-2
Peso molecular:
154.25
Beilstein/REAXYS Number:
1722455
EC Number:
203-378-7
MDL number:
MFCD00063204
UNSPSC Code:
12352100
PubChem Substance ID:
24856300
NACRES:
NA.22

Quality Level

100

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.)

functional group

hydroxyl

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

signalword

Warning

Hazard Classifications

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

Storage Class

10 - Combustible liquids

wgk_germany

WGK 2

flash_point_f

226.0 °F - closed cup

flash_point_c

107.78 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificados de análisis (COA)

Lot/Batch Number
SHBQ1123
SHBN0144
SHBM9268
SHBM8860
SHBL5868

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M0120000

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(±)-Citronellal ≥95.0% (GC)

Sigma-Aldrich

27470

(±)-Citronellal

Geranyl bromide 95%

Sigma-Aldrich

329118

Geranyl bromide

Citral natural, ≥96%, FCC, FG

Sigma-Aldrich

W230316

Citral

D-Carvone ≥96%, FG

Sigma-Aldrich

W224928

D-Carvone

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
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
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
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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