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
SMILES string
C[C@@H](CC\C=C(/C)C)CC(O)=O
InChI key
GJWSUKYXUMVMGX-VIFPVBQESA-N
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
Quality Level
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.
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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