1,5-dimethyl 3-hydroxypentanedioate

• ChemBase ID: 145557
• Molecular Formular: C7H12O5
• Molecular Mass: 176.16718
• Monoisotopic Mass: 176.06847348
• SMILES: COC(=O)CC(CC(=O)OC)O
• Canonical SMILES: COC(=O)CC(CC(=O)OC)O
• InChI: InChI=1S/C7H12O5/c1-11-6(9)3-5(8)4-7(10)12-2/h5,8H,3-4H2,1-2H3
• InChIKey: CUPGMRSSZADEIW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,5-dimethyl 3-hydroxypentanedioate
• IUPAC Traditional name: 1,5-dimethyl 3-hydroxypentanedioate
• Synonyms: Dimethyl 3-hydroxyglutarate; Dimethyl 3-hydroxypentanedioate; 3-Hydroxy-pentanedioic Acid Dimethyl Ester; Dimethyl 3-hydroxyglutarate; NSC 30047; 3-Hydroxyglutaric Acid Dimethyl Ester; 3-羟基戊二酸二甲酯

Database IDs

• CAS Number: 7250-55-7
• MDL Number: MFCD00042841
• Beilstein Number: 1776666
• PubChem SID: 24879287; 162239762; 24850190
• PubChem CID: 232491

CALCULATED PROPERTIES

• Acid pKa: 14.737501
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.7370298
• LogD (pH = 7.4): -0.7370298
• Log P: -0.7370298
• Molar Refractivity: 39.0377 cm^3
• Polarizability: 15.942755 Å^3
• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White to Pale Yellow Oil
• Boiling Point: 139-140 °C/8 mmHg(lit.)
• Flash Point: 113 °C; 235.4 °F
• Density: 1.192 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.442(lit.); n20/D 1.445

Safety Information

• Storage Condition: Refrigerator
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves

Product Information

• Purity: ≥97.0% (GC); 90%; 98%
• Grade: purum
• Linear Formula: CH3OCOCH2CH(OH)CH2COOCH3

DETAILS

Sigma Aldrich - 166979

Packaging
5 g in glass bottle

Sigma Aldrich - 55275

Other Notes
Starting material for the synthesis of pimaricin1

Toronto Research Chemicals - H942590

Glutaric Acid derivative

REFERENCES

• Higashi, K., et al.: Chem. Pharm. Bull., 40, 1042 (1992)
• Wilde, J., et al.: Eur. J. Biochem., 221, 463 (1992)