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375233

Sigma-Aldrich

Dimethyl 3-methylglutarate

99%

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About This Item

Linear Formula:
CH3CH(CH2CO2CH3)2
CAS Number:
19013-37-7
Molecular Weight:
174.19
MDL number:
MFCD00075608
UNSPSC Code:
12352100
PubChem Substance ID:
24863375
NACRES:
NA.22

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.)

functional group

ester

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.[1]

Application

Building block for chemoenzymatic asymmetric synthesis.[2][3]
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.[2] It may be used in the preparation of optically active form of verrucarinic acid derivative.[4] It may be used as building block for chemoenzymatic asymmetric synthesis.[2][3]

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

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Certificates of Analysis (COA)

Lot/Batch Number
BGBC2963V
MKAA0550
80496MJ
03523BH
12021JE

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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)
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)
Tetrahedron, 44, 1477-1477 (1988)
Chemoenzymatic synthesis of (R)-and (S)-4-amino-3-methylbutanoic acids.
Andruszkiewicz R, et al.
Synthetic Communications, 20, 159-166 (1990)

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