(S)-3-hydroxylauric acid

Base Information

• Chemical Name: (S)-3-hydroxylauric acid
• CAS No.: 45162-48-9
• Molecular Formula: C₁₂H₂₄O₃
• Molecular Weight: 216.321
• Nikkaji Number: J61.162J
• Wikidata: Q27116740
• Metabolomics Workbench ID: 1436
• Mol file: 45162-48-9.mol

Synonyms:(S)-3-hydroxylauric acid;(3S)-3-hydroxydodecanoic acid;3S-hydroxy-dodecanoic acid;L-3-Hydroxydodecanoic acid;Dodecanoic acid, 3-hydroxy-, (S)-;beta-hydroxylaurate;beta-Hydroxydodecanoic acid;beta-hydroxydodecanoate;b-Hydroxylaurate;b-Hydroxydodecanoate;b-hydroxylauric acid;3-hydroxy-dodecanoate;DL-b-Hydroxydodecanoate;b-Hydroxydodecanoic acid;L-3-Hydroxylauric acid;(RS)-3-Hydroxylaurate;(S)-3-OH lauric acid;DL-beta-Hydroxydodecanoate;(S)-beta-OH lauric acid;DL-b-Hydroxydodecanoic acid;(RS)-3-Hydroxylauric acid;(S)-3-OH dodecanoic acid;(S)-beta-hydroxylauric acid;(S)-beta-OH dodecanoic acid;(S)-3-hydroxydodecanoic acid;DL-beta-Hydroxydodecanoic acid;SCHEMBL6236754;(S)-beta-hydroxydodecanoic acid;CHEBI:36210;LMFA01050252;Q27116740

Chemical Property of (S)-3-hydroxylauric acid

Chemical Property:

• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 216.17254462
• Heavy Atom Count: 15
• Complexity: 157

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCCCCCC(CC(=O)O)O
• Isomeric SMILES: CCCCCCCCC[C@@H](CC(=O)O)O

Technology Process of (S)-3-hydroxylauric acid

There total 11 articles about (S)-3-hydroxylauric 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:

C12H24O2 (933486-31-8) → (3R)-(-)-3-Hydroxydodecanoic acid (28254-78-6,53941-38-1) + (3S)-3-hydroxydodecanoic acid (45162-48-9,53941-38-1)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; In water; tert-butyl alcohol; at 20 ℃; for 16h; Overall yield = 1.77 g; Inert atmosphere;

DOI:10.3390/md11072382

Reference yield:

caprinaldehyde (112-31-2) → (3R)-(-)-3-Hydroxydodecanoic acid (28254-78-6,53941-38-1) + (3S)-3-hydroxydodecanoic acid (45162-48-9,53941-38-1)

Guidance literature:

Multi-step reaction with 4 steps

1: allylmagnesium bromide / diethyl ether / 1 h / -42 - 20 °C / Inert atmosphere

2: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 32 h / 20 °C / Inert atmosphere

3: sodium periodate / water; tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

4: sodium chlorite; sodium dihydrogenphosphate / water; tert-butyl alcohol / 16 h / 20 °C / Inert atmosphere

With sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; allylmagnesium bromide; In tetrahydrofuran; diethyl ether; water; acetone; tert-butyl alcohol;

DOI:10.3390/md11072382

Reference yield:

C13H28O3 → (3R)-(-)-3-Hydroxydodecanoic acid (28254-78-6,53941-38-1) + (3S)-3-hydroxydodecanoic acid (45162-48-9,53941-38-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium periodate / water; tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

2: sodium chlorite; sodium dihydrogenphosphate / water; tert-butyl alcohol / 16 h / 20 °C / Inert atmosphere

With sodium chlorite; sodium periodate; sodium dihydrogenphosphate; In tetrahydrofuran; water; tert-butyl alcohol;

DOI:10.3390/md11072382

upstream raw materials:

caprinaldehyde

bromoacetic acid tert-butyl ester

bromoacetic acid methyl ester

sodium ethyl acetylacetate enolate

Downstream raw materials:

tert.-Butyl-O-(N-benzyloxycarbonyl-L-valyl)-L-3-hydroxydodecanoat