364428
(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:
Molecular Weight:
170.25
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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.)
functional group
carboxylic acid
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.
Signal Word
Warning
Hazard Statements
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
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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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