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209465

Sigma-Aldrich

4-Hexylresorcinol

98%

Synonym(s):

Antascarin, Ascarinol, 4-Hexyl-1,3-dihydroxybenzene

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About This Item

Linear Formula:
CH3(CH2)5C6H3-1,3-(OH)2
CAS Number:
136-77-6
Molecular Weight:
194.27
Beilstein:
2048312
EC Number:
205-257-4
MDL number:
MFCD00002284
UNSPSC Code:
12352100
PubChem Substance ID:
24852569
NACRES:
NA.22

Assay

98%

bp

333-335 °C (lit.)

mp

65-67 °C (lit.)

solubility

water: soluble 2000 part(lit.)
acetone: soluble(lit.)
alcohol: soluble(lit.)
chloroform: soluble(lit.)
diethyl ether: soluble(lit.)
petroleum ether: slightly soluble(lit.)
vegetable oils: soluble(lit.)

SMILES string

CCCCCCc1ccc(O)cc1O

InChI

1S/C12H18O2/c1-2-3-4-5-6-10-7-8-11(13)9-12(10)14/h7-9,13-14H,2-6H2,1H3

InChI key

WFJIVOKAWHGMBH-UHFFFAOYSA-N

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Application

4-Hexylresorcinol is used as the starting material to synthesize a potent immune suppressor, celastramycin A. It is a precursor to prepare resorcinol-sn-glycerol derivatives, that exhibit high affinity for cannabinoid type 1 receptor. It can also be incorporated as a linker while building catenanes.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H319,H411

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

388.4 °F

Flash Point(C)

198 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Yunbin Hao et al.
Molecules (Basel, Switzerland), 23(9) (2018-08-31)
A method for the rapid determination of 4-hexylresorcinol (4-HR) residue in shrimp by solid phase extraction (SPE) ultra-high performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) was established. 4-HR was extracted twice with methanol, and the extract was formulated into methanol-water solution
E Arias et al.
Journal of food science, 72(8), C422-C429 (2007-11-13)
The effects of ascorbic acid (AA) and 4-hexylresorcinol (4-HR) on pear polyphenoloxidase (PPO) activity and stability have been investigated in vitro. AA does not interact directly with PPO but prevents browning by reducing oxidized substrates. The 4-HR exerts a dual
Tobias Mann et al.
International journal of molecular sciences, 19(3) (2018-03-03)
Tyrosinase inhibitors are of great clinical interest as agents for the treatment of hyperpigmentary disorders; however, most compounds described in the literature lack clinical efficiency due to insufficient inhibitory activity against human tyrosinase (hTyr). Recently, we reported that thiazolyl resorcinols
E Arias et al.
Journal of food science, 72(9), C464-C470 (2007-11-24)
We have investigated the mechanism of action of 4-hexylresorcinol (4-HR) and ascorbic acid (AA) on the polyphenol oxidase (PPO) catalyzed oxidation of phenolic substrates. Incubation of PPO with 4-HR diminishes strongly PPO activity. This effect can be erroneously interpreted, due
Revised structure and synthesis of celastramycin a, a potent innate immune suppressor.
Kikuchi H, et al.
Organic Letters, 11(8), 1693-1695 (2009)
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