All Photos(1)
Synonym(s):
(S)-(−)-3,7-Dimethyl-6-octenoic acid
Linear Formula:
(CH3)2C=CHCH2CH2CH(CH3)CH2CO2H
CAS Number:
Molecular Weight:
170.25
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
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.
Signal Word
Warning
Hazard Statements
Hazard Classifications
Skin Irrit. 2
WGK
WGK 3
Flash Point(F)
>235.4 °F
Flash Point(C)
> 113 °C
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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