63685
(−)-Menthyloxyacetic acid
purum, ≥98.0% (sum of enantiomers, GC)
Synonym(s):
(−)-Menthyl carboxymethyl ether
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About This Item
Empirical Formula (Hill Notation):
C12H22O3
CAS Number:
Molecular Weight:
214.30
EC Number:
254-857-2
UNSPSC Code:
12352112
PubChem Substance ID:
Beilstein/REAXYS Number:
2444474
MDL number:
grade
purum
assay
≥98.0% (sum of enantiomers, GC)
optical activity
[α]20/D −93±3°, c = 10% in ethanol
optical purity
enantiomeric ratio: ≥98.25:1.75 (GC)
refractive index
n20/D 1.4672 (lit.)
bp
163-164 °C/10 mmHg (lit.)
mp
52-55 °C (lit.)
density
1.01 g/mL at 20 °C (lit.)
SMILES string
CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OCC(O)=O
InChI
1S/C12H22O3/c1-8(2)10-5-4-9(3)6-11(10)15-7-12(13)14/h8-11H,4-7H2,1-3H3,(H,13,14)/t9-,10+,11-/m1/s1
InChI key
CILPHQCEVYJUDN-OUAUKWLOSA-N
Application
(-)-Menthyloxyacetic acid can be used as a reactant to synthesize pentavalent organobismuth bis(-)menthyloxyacetate derivatives by reacting with corresponding organobismuth reagents via C-arylation reaction. It can also be used in the preparation of chiral cellulose (-)-menthyloxyacetate (a cellulose ester), which may be utilized as a membrane for the selective separation of bioactive molecules.
Other Notes
Reagent for the resolution of amines, amino acids, alcohols and phenols
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
235.4 °F - closed cup
flash_point_c
113 °C - closed cup
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
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R.E. Lehr et al.
The Journal of Organic Chemistry, 50, 98-98 (1985)
K. Iwamoto et al.
Journal of the American Chemical Society, 115, 3997-3997 (1993)
Tailored cellulose esters: synthesis and structure determination
Liebert TF and Heinze T
Biomacromolecules, 6(1), 333-340 (2005)