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16-HYDROXYHEXADECANOIC ACID

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16-HYDROXYHEXADECANOIC ACID Basic information

Product Name:
16-HYDROXYHEXADECANOIC ACID
Synonyms:
  • JUNIPERIC ACID
  • Hexadecanoic acid, 16-hydroxy-
  • 16-HYDROXYHEXADECANOIC ACID
  • 16-HYDROXYPALMITIC ACID
  • 16-hydroxy-hexadecanoicaci
  • 16-Hydroxyhexadecanoic acid, 97+%
  • 16-Hydroxyhexadecanoicacid,98%
  • 16-Hydroxypalmitic acid, Juniperic acid
CAS:
506-13-8
MF:
C16H32O3
MW:
272.42
EINECS:
208-028-7
Product Categories:
  • omega-Functional Alkanols, Carboxylic Acids, Amines & Halides
  • omega-Hydroxycarboxylic Acids
  • 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
Mol File:
506-13-8.mol
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16-HYDROXYHEXADECANOIC ACID Chemical Properties

Melting point:
94-98 °C(lit.)
Boiling point:
414.4±18.0 °C(Predicted)
Density 
0.956±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMF: 20 mg/ml; DMSO: 20 mg/ml; DMSO:PBS(pH 7.2) (1:2): 0.33 mg/ml; Ethanol: 2.5 mg/ml
form 
Crystalline Powder
pka
4.78±0.10(Predicted)
color 
White
BRN 
1783998
InChI
InChI=1S/C16H32O3/c17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(18)19/h17H,1-15H2,(H,18,19)
InChIKey
UGAGPNKCDRTDHP-UHFFFAOYSA-N
SMILES
C(O)(=O)CCCCCCCCCCCCCCCO
LogP
4.904 (est)
CAS DataBase Reference
506-13-8(CAS DataBase Reference)
EPA Substance Registry System
16-Hydroxypalmitic acid (506-13-8)
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Safety Information

Risk Statements 
36/37/38
Safety Statements 
22-24/25
WGK Germany 
3
TSCA 
Yes
HS Code 
29181998

MSDS

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16-HYDROXYHEXADECANOIC ACID Usage And Synthesis

Description

16-hydroxy Hexadecanoic acid is a metabolite of the saturated fatty acid palmitic acid (16:0) that has been hydroxylated on its terminal (ω) carbon. It is produced by ω-hydroxylation of palmitic acid by cytochrome P450 in both plants and animals. In plants, it is commonly a component of cutin.

Chemical Properties

white crystalline solid

Uses

16-Hydroxyhexadecanoic acid was used in the synthesis of dihydroxypalmitic acids. It was also used to induce the expression of two GRP genes of Arabidopsis thaliana, AtGRP5 and AtGRP23.

Application

16-Hydroxyhexadecanoic acid can be used to:
(1) Oxidative reactions: Cell lysates and intact cells of Escherichia coli JM101 recombinant, which synthesises the cyp102 gene for cytochrome P450BM-3 monooxygenase, biotransform 16-hydroxyhexa-decanoic acid into 1, 16-hexadecanedioic acid. a small amount of intermediate product accumulation accompanies the oxidation of 16-hydroxyhexadecanoic acid. hydroxyhexadecanoic acid oxidation is accompanied by the accumulation of a small amount of intermediate products. The by-products also include 13.16-dihydroxyhexadecanoic acid and 12,16-dihydroxyhexadecanoic acid[1].
(2) 16-hydroxyhexadecanoic acid ethyl ester was synthesised from 16-hexadecanolactone by an intramolecular ester exchange reaction with PEG-lipase[2].
(3) Lactonisation reaction: It has been demonstrated that Mucor javanicus L46 and Mucor miehei catalyse the lactonisation reaction of 15-hydroxypentadecanoic and 16- hydroxyhexadecanoic acids to appropriate macrocyclic mono- and oligolactones[3].

Definition

ChEBI: 16-hydroxyhexadecanoic acid is an omega-hydroxy-long-chain fatty acid that is hexadecanoic acid (also known as palmitic acid) which is substituted at position 16 by a hydroxy group. It is a key monomer of cutin in the plant cuticle. It has a role as a plant metabolite. It is an omega-hydroxy-long-chain fatty acid and a hydroxypalmitic acid. It is a conjugate acid of a 16-hydroxyhexadecanoate.

References

[1] S. SCHNEIDER. Production Of Alkanedioic Acids By Cytochrome P450Bm-3 Monooxygenase: Oxidation Of 16-Hydroxyhexadecanoic Acid To Hexadecane-1, 16-Dioic Acid[J]. Biocatalysis and Biotransformation, 1999. DOI:10.3109/10242429909040113.
[2] YOH KODERA . Lactone synthesis from 16-hydroxyhexadecanoic acid ethyl ester in organic solvents catalyzed with polyethylene glycol-modified lipase[J]. Journal of biotechnology, 1993. DOI:10.1016/0168-1656(93)90162-G.
[3] U. ANTCZAK . Enzymatic lactonization of 15-hydroxypentadecanoic and 16-hydroxyhexadecanoic acids to macrocyclic lactones[J]. Enzyme and Microbial Technology, 1991. DOI:10.1016/0141-0229(91)90095-R.

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