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About This Item
Linear Formula:
CH3CH(CH2CO2CH3)2
CAS Number:
Molecular Weight:
174.19
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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assay
99%
form
liquid
refractive index
n20/D 1.425 (lit.)
bp
110 °C/19 mmHg (lit.)
density
1.052 g/mL at 25 °C (lit.)
SMILES string
COC(=O)CC(C)CC(=O)OC
InChI
1S/C8H14O4/c1-6(4-7(9)11-2)5-8(10)12-3/h6H,4-5H2,1-3H3
InChI key
YIJLMTNDXYVGPQ-UHFFFAOYSA-N
General description
Dimethyl 3-methylglutarate is an ester. It participates in the synthesis of (R,Z)- muscenone, a valuable perfume ingredient.
Application
Building block for chemoenzymatic asymmetric synthesis.
Dimethyl 3-methylglutarate may be used in the synthesis of (R)- and (S)-4-amino-3-methylbutanoic acids, via initial enantioselective hydrolysis with pig liver esterase. It may be used in the preparation of optically active form of verrucarinic acid derivative. It may be used as building block for chemoenzymatic asymmetric synthesis.
Storage Class
10 - Combustible liquids
wgk_germany
WGK 3
flash_point_f
206.6 °F - closed cup
flash_point_c
97.00 °C - closed cup
ppe
Eyeshields, Gloves
Certificates of Analysis (COA)
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Synthesis of Verrucarin A and 3a-Hydroxyverrucarin A from Verrucarol and Diacetoxyscripenol (Anguidine). 39th Communication on Verrucarins and Roridins.
Mohr P, et al.
Helvetica Chimica Acta, 65(5), 1412-1417 (1982)
An efficient route to the musk odorant (< i> R</i>,< i> Z</i>)-5-muscenone via base-metal-catalysis.
Lehr K and Furstner A.
Tetrahedron, 68(37), 7695-7700 (2012)
Chemoenzymatic synthesis of (R)-and (S)-4-amino-3-methylbutanoic acids.
Andruszkiewicz R, et al.
Synthetic Communications, 20, 159-166 (1990)
Tetrahedron, 44, 1477-1477 (1988)
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