28254-78-6

Basic information

• Product Name: 3-(R)-Hydroxydodecanoic acid
• Synonyms: (-)-3-Hydroxylauric acid;(R)-3-Hydroxydodecanoic acid;[R,(-)]-3-Hydroxylauric acid;3-(R)-Hydroxydodecanoic acid;[S,(+)]-3-Hydroxylauric acid;L-3-Hydroxydodecanoic acid;L-3-Hydroxylauric acid;9-Hydroxydodecanoic acid
• CAS NO: 28254-78-6
• Molecular Formula: C₁₂H₂₄O₃
• Molecular Weight: 0
• Mol File: 28254-78-6.mol
• Article Data: 18

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(R)-Hydroxydodecanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(R)-Hydroxydodecanoic acid(28254-78-6)
• EPA Substance Registry System: 3-(R)-Hydroxydodecanoic acid(28254-78-6)

Safety Data

• Hazardous Substances Data: 28254-78-6(Hazardous Substances Data)

Upstream product

• 112-31-2 caprinaldehyde 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 76835-64-8 methyl 3-oxododecanoate 
• 236412-69-4 (R)-(+)-1,2-epoxyundecane 
• 143-07-7 lauric acid 
• 99493-58-0 (4R)-tridec-1-en-4-ol 
• 112-44-7 undecylaldehyde 
• 17322-97-3 1,2-epoxyundecane 
• 1286707-66-1 fellutamide C 
• 125882-62-4 fellutamide B 
• 112-16-3 n-dodecanoyl chloride 
• 186383-49-3 2-(4-bromophenyl)-2-oxoethyl (R)-3-hydroxytetradecanoate 
• 182359-65-5 5-decanoyl-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 112-13-0 n-decanoyl chloride 

Downstream Products

• 76835-66-0 (R)-β-hydroxydodecanoic acid methyl ester 
• 125882-62-4 fellutamide B 
• 66997-68-0 (S)-methyl 3-hydroxydodecanoate 

Relevant articles and documents

Fellutamides A and B, cytotoxic peptides from a marine fish-possessing fungus Penicillium fellutanum

Two cytotoxic peptides, fellutamides A and B, have been isolated from the cultured fungus Penicillium fellutanum Biourge which was isolated from the gastrointestine of the marine fish Apogon endekataenia Bleeker, and the structures were elucidated to be 1 and 2 by two-dimensional NMR and FAB MS/MS data.

Enzymatic Regio- And Enantioselective C-H Oxyfunctionalization of Fatty Acids

Directed evolution of a P450 hydroxylase (P450BSβ) achieves an engineered enzyme that is able to catalyze C-H oxyfunctionalization of fatty acids (FAs) in a highly regio- and enantioselective fashion (>20:1 Cβ/Cα and > 99% ee in all cases). The biocatalyst displays high reactivity (TON up to 1540), takes inexpensive H2O2 as oxidant, and converts C11-C18 saturated FAs as well as naturally derived unsaturated oleic and linoleic acids to optically pure β-hydroxy FAs. Merging biocatalysis with chemical transformation, we further offer a chemoenzymatic strategy to access valuable FA derivatives bearing 1,3-diol, β-amino, β-lactone, and β-lactam functionalities in either enantiomeric form. Molecular docking studies provide a rationale for the regio- and enantioselectivity of this reaction.

Total synthesis of fellutamides, lipopeptide proteasome inhibitors. More sustainable peptide bond formation

Solution-phase syntheses of three bioactive natural products of mixed polypeptide-polyketide biogenesis, fellutamides A, B, and C, have been achieved. Three peptide bonds are generated without the use of coupling reagents in each synthesis of the fellutamides, which act against proteasomes.

Solution phase synthetic approach to fellutamide B

Abstract A convenient solution phase approach for the synthesis of fellutamide B with efficient purification techniques has been demonstrated on the molecule for the first time. The strategy involves the use of natural amino acids as starting materials and classical peptide coupling reactions. The synthesis has been achieved in 10 steps with overall yield of 26.7% making the synthesis facile.