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617-55-0 molecular structure
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1,4-dimethyl (2S)-2-hydroxybutanedioate

ChemBase ID: 70268
Molecular Formular: C6H10O5
Molecular Mass: 162.1406
Monoisotopic Mass: 162.05282342
SMILES and InChIs

SMILES:
C(=O)([C@H](CC(=O)OC)O)OC
Canonical SMILES:
COC(=O)C[C@@H](C(=O)OC)O
InChI:
InChI=1S/C6H10O5/c1-10-5(8)3-4(7)6(9)11-2/h4,7H,3H2,1-2H3/t4-/m0/s1
InChIKey:
YSEKNCXYRGKTBJ-BYPYZUCNSA-N

Cite this record

CBID:70268 http://www.chembase.cn/molecule-70268.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1,4-dimethyl (2S)-2-hydroxybutanedioate
IUPAC Traditional name
1,4-dimethyl (2S)-2-hydroxybutanedioate
Synonyms
Dimethyl (S)-2-hydroxysuccinate
Dimethyl L-malate
Dimethyl (S)-(-)-malate
Dimethyl L-malate
Dimethyl L-malate
(S)-2-羟基琥珀酸二甲酯
L-苹果酸二甲酯
(S)-(-)-苹果酸二甲酯
(S)-(-)-苹果酸二甲酯
L-苹果酸二甲酯
CAS Number
617-55-0
EC Number
432-310-0
MDL Number
MFCD00066215
Beilstein Number
1724363
PubChem SID
24863298
24845250
162035991
PubChem CID
10285815

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.443835  H Acceptors
H Donor LogD (pH = 5.5) -0.82185334 
LogD (pH = 7.4) -0.8218572  Log P -0.82185334 
Molar Refractivity 34.4134 cm3 Polarizability 14.136947 Å3
Polar Surface Area 72.83 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Boiling Point
104-108 °C/1 mmHg(lit.) expand Show data source
Flash Point
>113 °C expand Show data source
>235.4 °F expand Show data source
Density
1.223 g/mL at 25 °C(lit.) expand Show data source
1.232 g/mL at 20 °C(lit.) expand Show data source
Refractive Index
n20/D 1.435(lit.) expand Show data source
n20/D 1.441 expand Show data source
Optical Rotation
[α]20/D -6.5°, neat expand Show data source
[α]20/D -6.6±0.5°, neat expand Show data source
Storage Warning
IRRITANT expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
10-41-43 expand Show data source
Safety Statements
24-26-37/39-43 expand Show data source
TSCA Listed
false expand Show data source
GHS Pictograms
GHS02 expand Show data source
GHS05 expand Show data source
GHS07 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H226-H317-H318 expand Show data source
GHS Precautionary statements
P280-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥99.0% (sum of enantiomers, GC) expand Show data source
95+% expand Show data source
98% expand Show data source
Grade
puriss. expand Show data source
Linear Formula
CH3O2CCH2CH(OH)CO2CH3 expand Show data source
Empirical Formula (Hill Notation)
C6H10O5 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 374318 external link
Packaging
5, 25 g in glass bottle
Application
This chiral synthon has been used to prepare cytochrome P450 metabolites of arachidonic acid,1 and cyclic sulfolanes with HIV-1 protease inhibition potential.2
Sigma Aldrich - 02315 external link
Other Notes
Starting material used for the synthesis of many chiral building blocks1; Selective reduction of the 1-ester group with BH3.SMe22; Diastereoselective alkylation of C-33,4

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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