Lovastatin acid

Base Information

• Chemical Name: Lovastatin acid
• CAS No.: 75225-51-3
• Deprecated CAS: 76556-02-0,77285-87-1,77285-87-1
• Molecular Formula: C₂₄H₃₈O₆
• Molecular Weight: 422.562
• UNII: 5CLV35Y90C
• DSSTox Substance ID: DTXSID20873334
• Nikkaji Number: J399.042G
• Wikidata: Q24063271
• NCI Thesaurus Code: C77442
• Metabolomics Workbench ID: 148274
• ChEMBL ID: CHEMBL1201373
• Mol file: 75225-51-3.mol

Synonyms:L 154819;L-154,819;L-154819;lovestatin acid;mevinolinic acid;mevinolinic acid, (1S-(1alpha(betaS*,deltaS*),2alpha,6beta,8beta(R*),8aalpha))-isomer;mevinolinic acid, aluminum salt (3:1);mevinolinic acid, calcium salt (2:1);mevinolinic acid, monoammonium salt, 1S-(1alpha(betaS*),2alpha,6beta,8beta(R*),8aalpha)-isomer;mevinolinic acid, monosodium salt;mevinolinic acid, monosodium salt, (1S-(1alpha(betaS*,deltaS*),2alpha,6beta,8beta(R*),8aalpha))-isomer

Chemical Property of Lovastatin acid

Chemical Property:

• Vapor Pressure: 5.09E-17mmHg at 25°C
• Melting Point: 140 - 143oC
• Boiling Point: 602.3°Cat760mmHg
• PKA: 4.31±0.10(Predicted)
• Flash Point: 199.1°C
• PSA: 106.89000
• Density: 1.14g/cm³
• LogP: 2.38090
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated), Water (Slightly)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 422.26683893
• Heavy Atom Count: 30
• Complexity: 654

Purity/Quality:

99% ^*data from raw suppliers

Lovastatin Hydroxy Acid, Sodium Salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC(CC(CC(=O)O)O)O)C
• Isomeric SMILES: CC[C@H](C)C(=O)O[C@H]1C[C@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@H](C[C@H](CC(=O)O)O)O)C

Technology Process of Lovastatin acid

There total 6 articles about Lovastatin 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:

lovastatin (75330-75-5,79952-44-6) → lovastatin acid (75225-51-3,137767-34-1,76556-02-0,77285-87-1) + (4R,6R)-4-hydroxy-6-(2-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)ethyl)tetrahydro-2H-pyran-2-one (151006-15-4,79952-42-4,76343-78-7,81739-25-5) + (3R,5R)-3,5-dihydroxy-7-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)heptanoic acid (132748-10-8)

Guidance literature:

lovastatin; With methanol; sodium hydroxide; 2,6-di-tert-butyl-4-methyl-phenol; at 50 ℃; for 1h;

With methanol; ammonia; water; lovastatin esterase; at 40 ℃; for 43h; pH=9.5;

With hydrogenchloride; In methanol; water; at 12 ℃; pH=2.5;

Reference yield:

lovastatin (75330-75-5,79952-44-6) → lovastatin acid (75225-51-3,137767-34-1,76556-02-0,77285-87-1)

Guidance literature:

With sodium hydroxide; at 20 ℃; for 0.5h;

DOI:10.1002/1520-6017(200012)89:12<1594::AID-JPS11>3.0.CO;2-5

Reference yield:

(3R,5R)-3,5-dihydroxy-7-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)heptanoic acid (132748-10-8) → lovastatin acid (75225-51-3,137767-34-1,76556-02-0,77285-87-1)

Guidance literature:

With LovD; pH=7.9; Kinetics; aq. buffer;

upstream raw materials:

lovastatin

α-S-methylbutyryl-CoA

(3R,5R)-3,5-dihydroxy-7-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)heptanoic acid

α-S-methylbutyryl-S-N-acetylcysteamine

Downstream raw materials:

C₄₁H₆₀N₄O₇Si

(4R,6R)-6-[2-((1S,2S,6R,8S,8aR)-8-[((4-{1-[7-(hydroxyamino)-7-oxoheptyl]-1H-1,2,3-triazol-4-yl}phenyl)carbamoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthyl)ethyl]-4-[(tert-butyldimethylsilyl)oxy]-3,4,5,6-tetrahydro-2H-pyran-2-one

(4R,6R)-4-hydroxy-6-(2-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)ethyl)tetrahydro-2H-pyran-2-one

(4R,6R)-6-[2-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthyl)ethyl]-4-[(tert-butyldimethylsilyl)oxy]-3,4,5,6-tetrahydro-2H-pyran-2-one

Refernces

• 1、 Harrison, Angela T.,Kriel, Frederik H.,Papathanasopoulos, Maria A.,Mosebi, Salerwe,Abrahams, Shaakira,Hewer, Raymond. "The evaluation of statins as potential inhibitors of the LEDGF/p75-HIV-1 integrase interaction". . p. 290 - 295. Retrieved 2015/03/04.
• 2、 Xie, Xinkai,Meehan, Michael J.,Xu, Wei,Dorrestein, Pieter C.,Tang, Yi. "Acyltransferase mediated polyketide release from a fungal megasynthase". supporting information; experimental part. p. 8388 - 8389. Retrieved 2009/10/24.