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| | 16-HYDROXYHEXADECANOIC ACID Basic information |
| | 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) |
| Risk Statements | 36/37/38 | | Safety Statements | 22-24/25 | | WGK Germany | 3 | | TSCA | Yes | | HS Code | 29181998 |
| | 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. | | 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. | | 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.
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| | 16-HYDROXYHEXADECANOIC ACID Preparation Products And Raw materials |
| Raw materials | 2H-Pyran, 2-[(15-bromo-2-pentadecyn-1-yl)oxy]tetrahydro--->10,12-Hexadecadiynoic acid, 16-hydroxy--->9-Hexadecenoic acid, 16-hydroxy-, (9Z)--->IHDA-->10-UNDECYNOIC ACID-->Undecanoic acid,10,11-dibromo--->1,12-Dibromododecane | | Preparation Products | 2-Hexanone, 4-hydroxy- (6CI,9CI)-->Hexadecanoic acid, 16-amino--->16-HEXADECANOLIDE-->1,16-HEXADECANEDIOL |
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