| Identification | More | [Name]
16-HYDROXYHEXADECANOIC ACID | [CAS]
506-13-8 | [Synonyms]
16-HYDROXYHEXADECANOIC ACID
16-HYDROXYPALMITIC ACID
JUNIPERIC ACID
16-hydroxy-hexadecanoicaci
16-Hydroxyhexadecanoic acid, 97+%
16-Hydroxyhexadecanoicacid,98%
16-Hydroxypalmitic acid, Juniperic acid | [EINECS(EC#)]
208-028-7 | [Molecular Formula]
C16H32O3 | [MDL Number]
MFCD00002750 | [Molecular Weight]
272.42 | [MOL File]
506-13-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystalline powder | [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) |
| Safety Data | Back Directory | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [TSCA ]
Yes | [HS Code ]
29181998 |
| Hazard Information | Back Directory | [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.1,2,3,4 In plants, it is commonly a component of cutin.5,2 | [Chemical Properties]
white crystalline powder | [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: A C16 omega-hydroxy fatty acid and key monomer of cutin in the plant cuticle. | [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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