(3R)-5-ethoxy-3-methyl-5-oxopentanoic acid

• ChemBase ID: 152110
• Molecular Formular: C8H14O4
• Molecular Mass: 174.19436
• Monoisotopic Mass: 174.08920893
• SMILES: CCOC(=O)C[C@H](C)CC(=O)O
• Canonical SMILES: C[C@H](CC(=O)O)CC(=O)OCC
• InChI: InChI=1S/C8H14O4/c1-3-12-8(11)5-6(2)4-7(9)10/h6H,3-5H2,1-2H3,(H,9,10)/t6-/m1/s1
• InChIKey: KAOCDZQOVPLMID-ZCFIWIBFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-5-ethoxy-3-methyl-5-oxopentanoic acid
• IUPAC Traditional name: (3R)-5-ethoxy-3-methyl-5-oxopentanoic acid
• Synonyms: (R)-Monoethyl 3-methylglutarate; (R)-mono-Ethyl 3-methylglutarate; (R)-1-Ethyl hydrogen 3-methylglutarate; 3-甲基戊二酸-(R)-单乙酯; (R)-1-乙基氢-3-甲基戊二酸酯

Database IDs

• CAS Number: 72594-19-5
• MDL Number: MFCD00077820
• Beilstein Number: 1562576
• PubChem SID: 162246255; 24885064
• PubChem CID: 11105851

CALCULATED PROPERTIES

• Acid pKa: 4.44767
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.25196576
• LogD (pH = 7.4): -2.0149975
• Log P: 0.8358068
• Molar Refractivity: 42.2043 cm^3
• Polarizability: 16.831173 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 74-76 °C/0.03 mmHg(lit.)
• Density: 1.076 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.437
• Optical Rotation: [α]20/D -1.3±0.2°, neat

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (sum of enantiomers, GC)
• Optical Purity: enantiomeric ratio: ~98:2 (GC)
• Empirical Formula (Hill Notation): C8H14O4

DETAILS

Sigma Aldrich - 67000

Other Notes
Enantiomerically pure monoesters of 3-methylglutarate allow the preparation of important chiral building blocks: synthesis of both enantiomers of β-methyl-γ-valerolactone1; synthesis of (R)-3-methylhexanol2; Kolbe synthesis of long-chain acids3; preparation of a verrucarinic building block4
Packaging
1 mL in glass bottle