2-Bromohexadecanoic acid

HCID 82145
NotesReactions
Substructure searchFind similar structures

Basic information

CAS
18263-25-7
Standard SMILES
CCCCCCCCCCCCCCC(Br)C(=O)O
InChIKey
DPRAYRYQQAXQPE-UHFFFAOYSA-N
Molecular formula
C16H31BrO2
Average molar mass
335.32 g/mol
Monoisotopic mass
334.15074233

Overview

2-bromohexadecanoic acid is a bromo fatty acid that is hexadecanoic (palmitic) acid carrying a single bromo substituent at position 2. It has a role as a fatty acid oxidation inhibitor. It is a 2-bromocarboxylic acid, a long-chain fatty acid, a straight-chain fatty acid and a bromo fatty acid. It is functionally related to a hexadecanoic acid.

Names & identifiers

Preferred name
2-Bromohexadecanoic acid
IUPAC
2-bromohexadecanoic acid
English name
2-Bromohexadecanoic acid
Molecular formula
C16H31BrO2
Molecular weight
335.32

Names & synonyms

2-Bromohexadecanoic acid18263-25-72-Bromopalmitic acid2-Bromopalmitatealpha-Bromopalmitic acid2-bromo-hexadecanoic acidDTXSID00377347EI4G5X28ZNSC-58378DTXCID8017734CHEBI:133152alpha-bromopalmitate
Show more names
A-BROMOPALMITIC ACIDα-Bromopalmitic acidBromohexadecanoicacid2-bromo-hexadecanoicaci2-Bromohexadecanoicacid97%
RefChem:467285242-137-0Hexadecanoic acid, 2-bromo-.alpha.-Bromopalmitic acidMFCD00004215CHEMBL118417UNII-7EI4G5X28ZEINECS 242-137-0

Database identifiers

CAS
18263-25-7
PubChem CID
82145
DTXSID
DTXSID0037734
ChEMBL
CHEMBL118417
ChEBI
CHEBI:133152
UNII
7EI4G5X28Z
EC Number
242-137-0
Nikkaji
J236.233C

Properties

Computed structural properties

XLogP
7.8
Topological polar surface area
37.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
14
Heavy atoms
19

Experimental & physicochemical properties

LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Halogenated fatty acids [FA0109]

Physicochemical properties

Melting point
52 · 52-54 °C
Boiling point
403.4 · 403.4±18.0 °C(Predicted)
Density
1.1985 · 1.1985 (rough estimate)
refractive index
1.465 · 1.4650 (estimate)
Flash point
113 °C · 113 °C
storage temp.
RT

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationStatus: Active Update: 26-03-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/27999
Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
hs_code
2915907098
risk_code
36/37/38
Signal word
Warning

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationSubstances which lower blood glucose levels.

Uses & manufacturing

General Manufacturing InformationHexadecanoic acid, 2-bromo-: INACTIVE
Applications · 3 items

Description2-Bromopalmitic acid (18263-25-7) inhibitsprotein S-palmitoylation.1 Blocks palmitic acid-induced increase in cAMP levels in human primary melanocytes expressing the melanocortin-1 receptor which undergoes an essential palmitoylation as a prerequisite for receptor signaling.2

Uses2-Bromopalmitic Acid is used in preparation of substituted purines and their analogs for inhibiting the expression of a pattern recognition receptor.

General DescriptionPPARδ (peroxisome proliferator-activated receptor, delta isoform) acts as a transcription factor for gene expression as well as playing a role in lipid metabolism regulation; activity of this receptor is ligand-regulated. 2-Bromohexadecanoic acid is a metabolically stable analoge of the fatty acid palmitic acid that has been shown to be a natural ligand for the PPARδ receptor. 2-Bromohexadecanoic acid has also been used in studies of fatty acid oxidation, palmitoylation, and glucose uptake.

Upstream & downstream products

Suppliers74 total

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
宁波君龙新材料有限公司0574 88552216 19032109277 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]

Additional notes

DefinitionChEBI: A bromo fatty acid that is hexadecanoic (palmitic) acid carrying a single bromo substituent at position 2.

Related reactions

8 records
New reaction record

Compound notes

Loading…