3,5-dihydroxy-3-methyl-Pentanoic acid

Base Information

• Chemical Name: 3,5-dihydroxy-3-methyl-Pentanoic acid
• CAS No.: 150-97-0
• Molecular Formula: C₆H₁₂O₄
• Molecular Weight: 148.159
• UNII: S5UOB36OCZ
• DSSTox Substance ID: DTXSID5040546
• Nikkaji Number: J5.859I
• Wikipedia: Mevalonic_acid
• Wikidata: Q27088641
• Mol file: 150-97-0.mol

Synonyms:Hiochicacid (6CI); Valeric acid, 3,5-dihydroxy-3-methyl- (8CI); (3RS)-Mevalonic acid;(?à)-Mevalonic acid;2,4-Dideoxy-3-C-methylpentonic acid; 3,5-Dihydroxy-3-methylpentanoic acid;3,5-Dihydroxy-3-methylvaleric acid; DL-Mevalonic acid; MK 91; MVA; MVS;Mevalonic acid; RS-Mevalonic acid; b,d-Dihydroxy-b-methylvaleric acid

Chemical Property of 3,5-dihydroxy-3-methyl-Pentanoic acid

Chemical Property:

• Vapor Pressure: 8.91E-07mmHg at 25°C
• Melting Point: 151-152 °C(Solv: benzene (71-43-2))
• Boiling Point: 364.1°Cat760mmHg
• PKA: 4.33±0.10(Predicted)
• Flash Point: 188.2°C
• PSA: 77.76000
• Density: 1.263g/cm³
• LogP: -0.40550
• Storage Temp.: 2-8°C
• XLogP3: -1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 148.07355886
• Heavy Atom Count: 10
• Complexity: 123

Purity/Quality:

98%,99%, ^*data from raw suppliers

(RS)-Mevalonic acid lithium salt ≥96.0% (GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCO)(CC(=O)O)O
• Recent ClinicalTrials: Safety Study of MVA Smallpox Vaccine in Subjects With a History of Atopic Dermatitis (AD)
• Uses: Precursor in the biosynthesis of cholesterol. Occurs in equilibrium with the d-lactone

Technology Process of 3,5-dihydroxy-3-methyl-Pentanoic acid

There total 8 articles about 3,5-dihydroxy-3-methyl-Pentanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

mevalonolactone (674-26-0,503-48-0) → D,L-mevalonic acid (150-97-0,690-72-2,17817-88-8,32451-23-3)

Guidance literature:

With water; potassium hydroxide; at 40 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.ejmech.2014.11.040 DOI:10.1016/j.ejmech.2014.11.040

Reference yield:

→ D,L-mevalonic acid (150-97-0,690-72-2,17817-88-8,32451-23-3)

Guidance literature:

With sodium hydroxide;

DOI:10.1021/ja01566a080

Reference yield:

3-Hydroxy-3-methyl-6,6-diphenyl-hex-5-enoic acid ethyl ester → D,L-mevalonic acid (150-97-0,690-72-2,17817-88-8,32451-23-3)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH / methanol / Ambient temperature

2: (i) O₃, CH₂Cl₂, MeOH, (ii) NaBH₄, H₂O

With sodium hydroxide; In methanol;

upstream raw materials:

meglutol

3-Hydroxy-3-methyl-5-hexenoic acid

3-Hydroxy-3-methyl-6.6-diphenyl-hexen-⁽⁵⁾-saeure

1,1-diallylethanol

Downstream raw materials:

(S)-Mevalonsaeure

elymoclavine

mevalonic acid

phenyl 2-(4-methyl-2-oxo-1,3-dioxan-4-yl)acetate

Refernces

• 1、 -. "Process For The Production Of Isoprenol From Mevalonate Employing a Diphosphomevalonate Decarboxylae". Paragraph 0103. . Retrieved 2016/03/04.