4617-33-8

Basic information

• Product Name: 15-HYDROXYPENTADECANOIC ACID
• Synonyms: 15-HYDROXYPENTADECANOIC ACID;OMEGA-HYDROXY C15:0;15-Hydroxypentadecanoic acid, 99+%;15-Hydroxypentadecanoic acid 97%
• CAS NO: 4617-33-8
• Molecular Formula: C₁₅H₃₀O₃
• Molecular Weight: 258.4
• EINECS: 225-026-1
• Product Categories: omega-Functional Alkanols, Carboxylic Acids, Amines & Halides;omega-Hydroxycarboxylic Acids;C13 to C42+Fatty Acids;Carbonyl Compounds;Carboxylic Acids;Hydroxy fatty acids;Saturated fatty acids and derivatives;Biochemicals and Reagents;Building Blocks;C13 to C42+;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Fatty Acids and conjugates;Fatty Acyls;Hydroxy Fatty Acids;Lipids;Organic Building Blocks;CMLLYL
• Mol File: 4617-33-8.mol
• Article Data: 34

Chemical Properties

• Melting Point: 85-89 °C(lit.)
• Boiling Point: 400.9 °C at 760 mmHg
• Flash Point: 210.4 °C
• Appearance: white to light yellow crystalline powder
• Density: 0.963 g/cm³
• Vapor Pressure: 4.3E-08mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly, Sonicated), DMSO (Slightly)
• PKA: 4.78±0.10(Predicted)
• BRN: 1240100
• CAS DataBase Reference: 15-HYDROXYPENTADECANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 15-HYDROXYPENTADECANOIC ACID(4617-33-8)
• EPA Substance Registry System: 15-HYDROXYPENTADECANOIC ACID(4617-33-8)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 4617-33-8(Hazardous Substances Data)

Usage

Description

15-Hydroxypentadecanoic acid is a hydroxylated fatty acid, specifically an omega-hydroxy fatty acid, derived from pentadecanoic acid with a hydroxy group replacing one of the hydrogens of the terminal methyl group. It appears as a white to light yellow crystalline powder and is known for its involvement in the biosynthesis of pentadecanolide and its use in various chemical reactions and syntheses.

Uses

Used in Chemical Synthesis:
15-Hydroxypentadecanoic acid is used as a reagent for the synthesis of macrocyclic lactone musk compounds such as exaltolide and phoracantholide I, which are important in the fragrance industry due to their unique scent properties.
Used in Analytical Chemistry:
As an internal standard in the quantification of the formation of 11-hydroxylauric acid by gas chromatography, 15-Hydroxypentadecanoic acid helps ensure accurate and reliable results in chemical analyses.
Used in Radiolabeled Compound Synthesis:
In the synthesis of [16-14C]16DCA (Dicarboxylic acid) by a one-carbon elongation procedure at C15, 15-Hydroxypentadecanoic acid serves as a crucial intermediate, enabling the production of radiolabeled compounds for various research applications.
Used in Mass Spectrometry:
15-Hydroxypentadecanoic acid is used as an internal standard for the normalization of intensities in the mass spectra of plant cutin polymer, aiding in the accurate identification and quantification of various components within the polymer.
Used in Catalyst Research:
It may be used in the synthesis of 5-pentadecanolide on dealuminated HY zeolite, contributing to the study and development of new catalysts for chemical reactions.
Used in Pharmaceutical Research:
15-Hydroxypentadecanoic acid can also be utilized in the synthesis of fatty acid analogs of podophyllotoxin, which has potential applications in the development of new drugs and therapies.

InChI:InChI=1/C15H30O3/c16-14-12-10-8-6-4-2-1-3-5-7-9-11-13-15(17)18/h16H,1-14H2,(H,17,18)/p-1

Upstream product

• 116754-58-6 13-bromo-1-tridecylalcohol 
• 18424-76-5 dimethyl malonate sodium salt 
• 38223-29-9 12-oxo-15-pentadecanolide 
• 627-91-8 adipic acid monomethyl ester 
• 54894-30-3 11-acetoxyundecanoic acid 
• 1902-00-7 15-chloropentadecanoic acid 
• 23550-08-5 15-hydroxy-4-oxo-pentadecanoic acid 
• 92857-51-7 cis-15-Hydroxy-pentadecen-⁽²⁾-saeure 
• 57-57-8 β-Propiolactone 
• 91544-42-2 15-Hydroxy-pentadeca-10,12-diynoic acid 
• 629-98-1 erucyl alcohol 
• 616-01-3 13,14-dihydroxy-behenic acid 
• 92857-56-2 13-oxotridecyl acetate 
• 23550-09-6 13-hydroxy-1-methanesulfinyl-tridecan-2-one 

Downstream Products

• 76529-42-5 methyl 15-hydroxypentadecanoate 
• 97462-95-8 15-(Toluene-4-sulfonyloxy)-pentadecanoic acid 
• 106-02-5 pentadecanolide 
• 77172-46-4 isopropyl 15-hydroxypentadecanoate 
• 905302-64-9 tert-butyl 15-bromopentadecanoate 
• 16697-83-9 N-methyl-N-tosylacetamide 
• 7370-42-5 γ-pentadecalactone 
• 67400-04-8 Δ¹³-tetradecenol 
• 10411-39-9 methyl 15(Z)-octadecenoate 
• 99208-90-9 15-hexadecyn-1-oic acid 
• 1513888-73-7 (S)-15-hydroxy-N-(1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl)pentadecanamide 
• 78651-85-1 1-carboxytetradecyl 15-hydroxytetradecanoate 
• 659-76-7 1,17-dioxa-cyclodotriacontane-2,18-dione 
• 79134-83-1 1,17,33-trioxacyclooctatetracontane-2,18,34-trione 

Relevant articles and documents

ONE-STEP SYNTHESIS OF ω-HYDROXYCARBOXYLIC ACIDS BY THE REACTION OF ω-METALOXYLATED GRIGNARD REAGENTS WITH β-PROPIOLACTONES

ω-Metaloxylated Grignard reagents reacted with β-propiolactones chemo- and regioselectively in the presence of Li2CuCI4 to afford ω-hydroxycarboxylic acids in high yields.

SIMPLE SYNTHESIS OF 15-HYDROXYPENTADECANOIC ACID FROM 10-UNDECENOIC ACID

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Design, synthesis and pharmacology of aortic-selective acyl-CoA: Cholesterol O-acyltransferase (ACAT/SOAT) inhibitors

We describe our molecular design of aortic-selective acyl-coenzyme A:cholesterol O-acyltransferase (ACAT, also abbreviated as SOAT) inhibitors, their structure–activity relationships (SARs) and their pharmacokinetic (PK) and pharmacological profiles. The connection of two weak ligands—N-(2,6-diisopropylphenyl)acetamide (50% inhibitory concentration [IC50] = 8.6 μM) and 2-(methylthio)benzo[d]oxazole (IC50 = 31 μM)—via a linker comprising a 6 methylene group chains yielded a highly potent molecule, 9-(benzo[d]oxazol-2-ylthio)-N-(2,6-diisopropylphenyl)nonanamide (3h) that exhibited high potency (IC50 = 0.004 μM) toward aortic ACAT. This head-to-tail design made it possible to markedly enhance the activity to 2150- to 7750-fold and to discriminate the isoform-selectivity based on the double-induced fit mechanism. At doses of 1 and 3 mg/kg, 3h significantly decreased the lipid-accumulation areas in the aortic arch to 74 and 69%, respectively without reducing the plasma total cholesterol level in high fat- and cholesterol-fed F1B hamsters. Here, we demonstrate the antiatherosclerotic effect of 3h in vivo via its direct action on aortic ACAT and its powerful modulator of cholesterol level. This molecule is a potential therapeutic agent for the treatment of diseases involving ACAT-1 overexpression.

A macrolactonization approach to the total synthesis of the antimicrobial cyclic depsipeptide LI-F04a and diastereoisomeric analogues

The cyclic peptide core of the antifungal and antibiotic cyclic depsipeptide LI-F04a was synthesised by using a modified Yamaguchi macrolactonization approach. Alternative methods of macrolactonization (e.g., Corey-Nicolaou) resulted in significant epimerization of the C-terminal amino acid during the cyclization reaction. The D-stereochemistry of the alanine residue in the naturally occurring cyclic peptide may be required for the antifungal activity of this natural product.