16-Hydroxyhexadecanoic acid

HCID 10466
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Basic information

CAS
506-13-8
Standard SMILES
O=C(O)CCCCCCCCCCCCCCCO
InChIKey
UGAGPNKCDRTDHP-UHFFFAOYSA-N
Molecular formula
C16H32O3
Average molar mass
272.42 g/mol
Monoisotopic mass
272.23514488

Overview

16-hydroxyhexadecanoic acid is an -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.

Names & identifiers

Preferred name
16-Hydroxyhexadecanoic acid
IUPAC
16-hydroxyhexadecanoic acid
English name
16-HYDROXYHEXADECANOIC ACID
Molecular formula
C16H32O3
Molecular weight
272.42

Names & synonyms

16-Hydroxyhexadecanoic acid506-13-8Juniperic acid16-HYDROXYPALMITIC ACIDPalmitic acid, 16-hydroxy-omega-Hydroxypalmitic acid7IPP3U0F3INSC-159292DTXSID6060133CHEBI:55328RefChem:437511DTXCID8040858
Show more names
16-hydroxy-hexadecanoicacijunipericaci16-HYDROXYHEXADECANOI16-hydroxyhexadecanoateLactic Acid Impurity 12416-HydroxyhexadecanoicAcid>Hexadecanoic acid, 16-hydroxy-
208-028-7Hexadecanoic acid, 16-hydroxy-.omega.-Hydroxypalmitic acid16-hydroxy-hexadecanoic acidMFCD0000275016-hydroxy hexadecanoic acidhydroxy hexadecanoatehydroxy hexadecanoic acid

Database identifiers

CAS
506-13-8
PubChem CID
10466
DTXSID
DTXSID6060133
ChEMBL
CHEMBL4281719
ChEBI
CHEBI:55328
UNII
7IPP3U0F3I
EC Number
208-028-7
Nikkaji
J11.795A

Properties

Computed structural properties

XLogP
4.8
Topological polar surface area
57.5 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
15
Heavy atoms
19

Experimental & physicochemical properties

LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Hydroxy fatty acids [FA0105]
Melting Point94.00 to 98.00 °C. @ 760.00 mm Hg
Physical DescriptionSolid
Collision Cross Section168.99 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

Physicochemical properties

Melting point
94 · 94-98 °C(lit.)
Boiling point
414.4 · 414.4±18.0 °C(Predicted)
Density
0.956 · 0.956±0.06 g/cm3(Predicted)
storage temp.
2 · 2-8°C
solubility
20 mg/ml; · 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

Safety & regulation

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
hs_code
29181998
risk_code
36/37/38
safety_code
22-24/25

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

General Manufacturing InformationHexadecanoic acid, 16-hydroxy-: ACTIVE
Applications · 2 items

Description16-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.

Uses16-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.

Upstream & downstream products

Suppliers100 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
上海策嵘生物科技有限公司[email protected]
Additional notes · 1 item

DefinitionChEBI: 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.

Related reactions

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Compound notes

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