16-HYDROXYHEXADECANOIC ACID
Synonym(s):16-Hydroxypalmitic acid;Juniperic acid
- CAS NO.:506-13-8
- Empirical Formula: C16H32O3
- Molecular Weight: 272.42
- MDL number: MFCD00002750
- EINECS: 208-028-7
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-05-07 09:04:56
What is 16-HYDROXYHEXADECANOIC ACID?
Description
16-
Chemical properties
white crystalline solid
The Uses of 16-HYDROXYHEXADECANOIC ACID
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.
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.
What are the applications of 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].
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.
Properties of 16-HYDROXYHEXADECANOIC ACID
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 |
pka | 4.78±0.10(Predicted) |
form | Crystalline Powder |
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) |
CAS DataBase Reference | 506-13-8(CAS DataBase Reference) |
EPA Substance Registry System | 16-Hydroxypalmitic acid (506-13-8) |
Safety information for 16-HYDROXYHEXADECANOIC ACID
Computed Descriptors for 16-HYDROXYHEXADECANOIC ACID
InChIKey | UGAGPNKCDRTDHP-UHFFFAOYSA-N |
SMILES | C(O)(=O)CCCCCCCCCCCCCCCO |
New Products
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