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.)
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.
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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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