16-HYDROXYHEXADECANOIC ACID
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
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)
MSDS
- Language:English Provider:ACROS
- Language:English Provider:SigmaAldrich
- Language:English Provider:ALFA
16-HYDROXYHEXADECANOIC ACID Usage And Synthesis
Description
16-
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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