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10899

Sigma-Aldrich

Methyl 3-oxoheptanoate

Wacker Chemie AG, ≥96.0% (GC)

Synonym(s):

VEM, Methyl valerylacetate

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About This Item

Linear Formula:
CH3(CH2)3COCH2COOCH3
CAS Number:
Molecular Weight:
158.19
Beilstein/REAXYS Number:
1761380
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:

assay

≥96.0% (GC)

manufacturer/tradename

Wacker Chemie AG

bp

90-91 °C/15 hPa (lit.)

density

0.994 g/mL at 20 °C (lit.)

SMILES string

CCCCC(=O)CC(=O)OC

InChI

1S/C8H14O3/c1-3-4-5-7(9)6-8(10)11-2/h3-6H2,1-2H3

InChI key

CZTKGERSDUGZPQ-UHFFFAOYSA-N

General description

Methyl 3-oxoheptanoate undergoes Pechmann condensation with 2-methyl resorcinol using H2SO4 condensing agent to form 7-hydroxy-8-methyl coumarins.

Application

Methyl 3-oxoheptanoate was used in the synthesis of 3(R,S)-hydroxyheptanoic acid.

Other Notes

prices for bulk quantities on request

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

203.0 °F

flash_point_c

95 °C

ppe

Eyeshields, Gloves


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Modified coumarins. 28. Synthesis of spirosubstituted pyranocoumarins.
Nagorichna IV, et al.
Chemistry of Natural Compounds, 45(2), 152-157 (2009)
Mats Hamberg
The FEBS journal, 272(3), 736-743 (2005-01-27)
Incubations of [8(R)-2H]9(S)-hydroperoxy-10(E),12(Z)-octadecadienoic acid, [14(R)-2H]13(S)-hydroperoxy-9(Z),11(E)-octadecadienoic acid and [14(S)-2H]13(S)-hydroperoxy-9(Z),11(E)-octadecadienoic acid were performed with preparations of plant tissues containing divinyl ether synthases. In agreement with previous studies, generation of colneleic acid from the 8(R)-deuterated 9(S)-hydroperoxide was accompanied by loss of most of
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