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16-HYDROXYHEXADECANOIC ACID

16-HYDROXYHEXADECANOIC ACID Structure
CAS No.
506-13-8
Chemical Name:
16-HYDROXYHEXADECANOIC ACID
Synonyms
16-HYDROXYPALMITIC ACID;JUNIPERIC ACID;16-hydroxy-hexadecanoicaci;junipericaci;16-HYDROXYHEXADECANOI;16-hydroxyhexadecanoate;16-HYDROXYHEXADECANOIC ACID;16-HydroxyhexadecanoicAcid>Hexadecanoic acid, 16-hydroxy-;16-Hydroxyhexadecanoicacid,98%
CBNumber:
CB1488018
Molecular Formula:
C16H32O3
Molecular Weight:
272.42
MOL File:
506-13-8.mol
MSDS File:
SDS
Modify Date:
2024/5/7 9:04:56

16-HYDROXYHEXADECANOIC ACID 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)

SAFETY

Risk and Safety Statements

Risk Statements  36/37/38
Safety Statements  22-24/25
WGK Germany  3
TSCA  Yes
HS Code  29181998
NFPA 704
0
0 0

16-HYDROXYHEXADECANOIC ACID price More Price(4)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) 177490 16-Hydroxyhexadecanoic acid 98% 506-13-8 1G ₹3344.93 2022-06-14 Buy
Sigma-Aldrich(India) 177490 16-Hydroxyhexadecanoic acid 98% 506-13-8 5G ₹15977.7 2022-06-14 Buy
TCI Chemicals (India) H0675 16-Hydroxyhexadecanoic Acid min. 97.0 % 506-13-8 1G ₹5700 2022-05-26 Buy
TCI Chemicals (India) H0675 16-Hydroxyhexadecanoic Acid min. 97.0 % 506-13-8 5G ₹23400 2022-05-26 Buy
Product number Packaging Price Buy
177490 1G ₹3344.93 Buy
177490 5G ₹15977.7 Buy
H0675 1G ₹5700 Buy
H0675 5G ₹23400 Buy

16-HYDROXYHEXADECANOIC ACID Chemical Properties,Uses,Production

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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Hexadecanoic acid, 16-hydroxy- 16-HYDROXYHEXADECANOIC ACID 16-Hydroxyhexadecanoic acid, 97+% 16-Hydroxyhexadecanoicacid,98% 16-Hydroxypalmitic acid, Juniperic acid 16-hydroxyhexadecanoate 16-HydroxyhexadecanoicAcid> junipericaci 16-hydroxy-hexadecanoicaci 16-HYDROXYPALMITIC ACID JUNIPERIC ACID 16-HYDROXYHEXADECANOI 506-13-8 HOCH2CH214COOH C16H32O3 HOCH215CO2H 蠅-Functional Alkanols, Carboxylic Acids, Amines & Halides 蠅-Hydroxycarboxylic Acids Building Blocks C13 to C42+ Carbonyl Compounds Carboxylic Acids Organic Building Blocks 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