(R)-mevalonate

Base Information

• Chemical Name: (R)-mevalonate
• CAS No.: 1192-42-3
• Molecular Formula: C6H11O4-
• Molecular Weight: 116.117
• Hs Code.: 2932209090
• DSSTox Substance ID: DTXSID50415347
• Wikidata: Q27088561
• Mol file: 1192-42-3.mol

Synonyms:Acid, Mevalonic;Mevalonate;Mevalonic Acid

Chemical Property of (R)-mevalonate

Chemical Property:

• Boiling Point: 105-106 °C(Press: 5 Torr)
• PKA: 13.14±0.20(Predicted)
• PSA: 80.59000
• Density: 1.266±0.06 g/cm3(Predicted)
• LogP: -1.74020
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 147.06573383
• Heavy Atom Count: 10
• Complexity: 117

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CCO)(CC(=O)[O-])O
• Isomeric SMILES: C[C@@](CCO)(CC(=O)[O-])O
• General Description: Mevalonate is a key biosynthetic precursor involved in the production of monoterpene glucosides such as gentiopicroside and loganic acid in *Swertia caroliniensis*. It serves as the foundational molecule in the pathway leading to geranyl pyrophosphate, which is further metabolized into loganic acid and subsequently converted into gentiopicroside through ring cleavage. This demonstrates mevalonate's central role in the biosynthesis of iridoids, secoiridoids, and potentially indole alkaloids, linking it to broader secondary metabolite pathways in plants.

Technology Process of (R)-mevalonate

There total 12 articles about (R)-mevalonate 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: 91.0%

4-(1-ethoxy-ethoxy)-2-hydroxy-2,N-dimethyl-butyramide → (R)-2-methyl-2-hydroxy-γ-butyrolactone (1192-42-3)

Guidance literature:

With sulfuric acid; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0957-4166(99)00343-2

Reference yield:

(1R)-2-hydroxy-2-methyl-4-benzoyloxybutanoic acid → (R)-2-methyl-2-hydroxy-γ-butyrolactone (1192-42-3)

Guidance literature:

(1R)-2-hydroxy-2-methyl-4-benzoyloxybutanoic acid; With methanol; potassium carbonate; at 20 ℃; for 5.5h;

With hydrogenchloride; In methanol;

DOI:10.1002/jccs.200000006

Reference yield:

4-chloro-2-butanone (6322-49-2) + potassium cyanide (151-50-8) → 4,5-dihydro-3-hydroxy-3-methyl-2(3H)-furanone (1192-42-3)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/ja01132a515

upstream raw materials:

4-chloro-2-butanone

potassium cyanide

1-Hydroxy-3-butanone

Benzoic acid (R)-3-hydroxy-3-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-butyl ester

Downstream raw materials:

3-methyl-5H-furan-2-one

α-bromo-α-methyl-γ-butyrolactone

Refernces

Monoterpene biosynthesis. I. Occurrence and mevalonoid origin of gentiopicroside and loganic acid in Swertia caroliniensis

10.1021/bi00840a054

The research investigates the biosynthesis of gentiopicroside and loganic acid, two monoterpene glucosides found in the plant Swertia caroliniensis. The study aims to elucidate their biosynthetic pathways and confirm their mevalonoid origin. Key chemicals used include acetate-2-14C, mevalonate-2-14C, and mevalonate-2-3H-2-14C as labeled precursors. Through tracer experiments and various chemical transformations such as methylation, acetylation, and oxidation, the researchers demonstrated that both compounds originate from mevalonate. They also revised the structure of gentiopicroside based on chemical and spectral data, including double-resonance nuclear magnetic resonance studies. The results support a biogenetic scheme where mevalonate is converted to geranyl pyrophosphate, then to loganic acid, which undergoes ring cleavage to form gentiopicroside. The study concludes that loganic acid and its derivatives play a significant role as precursors for various iridoids and secoiridoids, and potentially for indole alkaloids, highlighting the interconnected biosynthetic pathways of these plant metabolites.

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