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364428

Sigma-Aldrich

(S)-(−)-Citronellic acid

98%

Synonym(s):

(S)-(−)-3,7-Dimethyl-6-octenoic acid

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About This Item

Linear Formula:
(CH3)2C=CHCH2CH2CH(CH3)CH2CO2H
CAS Number:
2111-53-7
Molecular Weight:
170.25
MDL number:
MFCD00134278
UNSPSC Code:
12352002
PubChem Substance ID:
24862429
NACRES:
NA.22

Assay

98%

form

liquid

optical activity

[α]25/D −8°, neat

refractive index

n20/D 1.453 (lit.)

bp

115-120 °C/0.4 mmHg (lit.)

density

0.926 g/mL at 25 °C (lit.)

SMILES string

C[C@@H](CC\C=C(/C)C)CC(O)=O

InChI

1S/C10H18O2/c1-8(2)5-4-6-9(3)7-10(11)12/h5,9H,4,6-7H2,1-3H3,(H,11,12)/t9-/m0/s1

InChI key

GJWSUKYXUMVMGX-VIFPVBQESA-N

Related Categories

Application

(S)-(-)-Citronellic acid may be used in the synthesis of trisubstituted piperidine substructures of the veratramine and jervine type, that can be building blocks for developing cyclopamine analogs.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315

Hazard Classifications

Skin Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

>235.4 °F - closed cup

Flash Point(C)

> 113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Philipp Heretsch et al.
Organic letters, 11(23), 5410-5412 (2009-11-04)
All four diastereomers of the trisubstituted piperidine-alkaloids of the veratramine and jervine type were synthesized with complete stereocontrol starting from enantiopure citronellic acids. The flexible, high-yielding, and scalable route described here will facilitate convergent syntheses and give access to analogues

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