HEXYLRESORCINOL

US Previously Marketed

First marketed in 1926

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H18O2
Molecular Weight	194.2701
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCC1=C(O)C=C(O)C=C1

InChI

InChIKey=WFJIVOKAWHGMBH-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.mhra.gov.uk/home/groups/par/documents/websiteresources/con2023661.pdf
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/international/hexylresorcinol.html

Hexylresorcinol is an organic compound with local anaesthetic, antiseptic and anthelmintic properties. It is available for use topically on small skin infections, or as an ingredient in throat lozenges. Hexylresorcinol may be used as a cosmetic biocide. Hexylresorcinol was introduced by Leonard as a urinary antiseptic with great possibilities. Used in alkaline solution it promised success in experiments in vitro. Boots Hexylresorcinol 2.4mg Throat Lozenges, marketed in UK, are used to relieve sore throat pain. Hexylresorcinol has being shown to be useful for the topical treatment of hyperpigmentation.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Arachidonate 5-lipoxygenase 52 Target ID: CHEMBL215 Sources: http://www.ncbi.nlm.nih.gov/pubmed/23871907	Inhibitor 8504	2.8 µM [IC50]
Parainfluenza virus type 3 1 Target ID: Parainfluenza virus type 3 Sources: http://www.ncbi.nlm.nih.gov/pubmed/26408353	Inhibitor 8504
Tyrosinase 41 Target ID: CHEMBL1973 Sources: http://www.ncbi.nlm.nih.gov/pubmed/23205541	Inhibitor 8504	94.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Sore throat 18 Sources: http://www.mhra.gov.uk/home/groups/par/documents/websiteresources/con2023661.pdf	Primary	Approved 8583	Boots Hexylresorcinol 2.4mg Throat Lozenges Blackcurrant Approved Use As an antiseptic and local anaesthetic for the relief of sore throat and its associated pain. Launch Date 2006
Hyperpigmentation 14 Sources: http://www.ncbi.nlm.nih.gov/pubmed/27391637	Primary	Preclinical	Unknown Approved Use Unknown
Respiratory tract infections 85 Sources: http://www.ncbi.nlm.nih.gov/pubmed/26408353	Curative	Preclinical	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1L2N8L
ABI Chem	AC1Q79ZK
Chemieliva Pharmaceutical Co., Ltd	PBCM1407503
ChemMol	99153870	http://www.chemmol.com/chemmol/99153870.html
Molcore	MC570269	https://www.molcore.com/product/7527-91-5
NovoSeek	24144
PubChem	24144	https://pubchem.ncbi.nlm.nih.gov/compound/24144
Smolecule	S517126	http://www.smolecule.com/products/s517126
THE BioTek	bt-257696	https://www.thebiotek.com/product/inhibitors/bt-257696

PubMed

Title	Date	PubMed
4-Hexylresorcinol inhibits transglutaminase-2 activity and has synergistic effects along with cisplatin in KB cells.	2011-06	21424127
Molecular modeling of peroxidase and polyphenol oxidase: substrate specificity and active site comparison.	2010-09-14	20957092
First evidence of laccase activity in the Pacific oyster Crassostrea gigas.	2010-04	20109560
The hunt for natural skin whitening agents.	2009-12-10	20054473
A fruit quality gene map of Prunus.	2009-12-08	19995417
Variations in IC(50) values with purity of mushroom tyrosinase.	2009-09-02	19865520
Abstracts of the 2008 ISSOL Meeting. August 24-29, 2008. Florence, Italy.	2009-08	19468860
Topical antiseptics for the treatment of sore throat block voltage-gated neuronal sodium channels in a local anaesthetic-like manner.	2009-08	19367399
An updated review of tyrosinase inhibitors.	2009-05-26	19582213
[Effect of a synthetic analogue of bacterial anabiosis autoinducers hexylresorcinol on the stability of membrane structures].	2009-04-23	19382705
[Modification of bacterial population structure on anti-lysozyme activity under the influence of hexylresorcinol].	2009-02-04	19189462
Identification of xenoestrogens in food additives by an integrated in silico and in vitro approach.	2009-01	19063592
Harnessing gene expression to identify the genetic basis of drug resistance.	2009	19888205
Solvent effects on the spectroscopic properties of 4-hexylresorcinol.	2008-11-15	18282797
Effect of natural antibrowning agents on color and related enzymes in fresh-cut Fuji apples as an alternative to the use of ascorbic acid.	2008-08	19241570
Effect of pyrophosphate and 4-hexylresorcinol pretreatment on quality of refrigerated white shrimp (Litopenaeus vannamei) kept under modified atmosphere packaging.	2008-04	18387125
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.	2008-04	18324785
Browning prevention by ascorbic acid and 4-hexylresorcinol: different mechanisms of action on polyphenol oxidase in the presence and in the absence of substrates.	2007-11	18034705
Ascorbic acid and 4-hexylresorcinol effects on pear PPO and PPO catalyzed browning reaction.	2007-10	17995596
[IR spectroscopic research on the impact of chemical analogues of autoregulatory d1 factors of microorganisms on structural changes in DNA].	2007-07-19	17633405
Oxyresveratrol as an antibrowning agent for cloudy apple juices and fresh-cut apples.	2007-04-04	17335224
[Long-term preservation of DNA in aqueous solutions in the presence of the chemical analogues of microbial autoregulators].	2006-11-10	17091589
[Influence of chemical analogues of microbial autoregulators on the sensitivity of DNA to UV radiation].	2006-11-10	17091588
Co-occurrence of the multicopper oxidases tyrosinase and laccase in lichens in sub-order peltigerineae.	2006-11	16950829
In vitro anthelmintic activity of Melia azedarach naturalized in Argentina.	2006-11	16941610
[Non-species-specific effects of unacylated homoserine lactone and hexylresorcinol, low molecular weight autoregulators, on the growth and development of bacteria].	2006-10-10	17025172
[A comparative study of the inducing effect of homoserine lactone and hexylresorcinol on phenotypic dissociation in bacteria].	2006-10-10	17025171
Use of experimental design methodology to prepare Maillard reaction products from glucose and cysteine inhibitors of polyphenol oxidase from eggplant (Solanum melongena).	2006-07-12	16819925
[Mechanisms of interaction between DNA and chemical analogues of microbial anabiosis autoinducers].	2005-12-01	16315980
[Determination of 4-hexylresorcinol residues in prawns and crabs].	2005-12	16440790
[Hexylresorcinol induces chromosome aberrations in mouse peripheral blood cells].	2005-08	16161624
[Effect of alkylhydroxybenzenes, microbial anabiosis inducers, on the structural organization of Pseudomonas aurantiaca DNA and on phenotypic dissociation induction].	2005-06-09	15938390
[Effect of a chemical analogue of autoinducers of microbial anabiosis on the Ca2+ response of mycelial fungi].	2005-02-04	15688932
Role of sulfites and 4-hexylresorcinol in microbial growth and melanosis prevention of deepwater pink shrimp (Parapenaeus longirostris) using a controlled atmosphere.	2005-01	15690809
Management of urinary tract infections: historical perspective and current strategies: Part 1--Before antibiotics.	2005-01	15592018
Inhibitory effects of hexylresorcinol and dodecylresorcinol on mushroom (Agaricus bisporus) tyrosinase.	2004-02	15106879
[Induction of SOS-response of cells exposed to autoregulatory factors of microorganisms].	2003-09	14582386
Effects of resveratrol and 4-hexylresorcinol on hydrogen peroxide-induced oxidative DNA damage in human lymphocytes.	2003-05	12797471
Polyphenol oxidases from latex of Hevea brasiliensis: purification and characterization.	2002-09	12169303
[The effect of anabiosis autoinducers on the bacterial genome].	2002-05-25	12024818
[Synthesis of anabiosis autoinducers in non-spore-forming bacteria as a mechanism regulating their activity in soil and subsoil sedimentary rocks].	2002-01-05	11763780
[Sensitization to resorcinol in a prescription verrucide preparation: unusual systemic clinical features and prevalence].	2001-05	11427795

Patents

Sample Use Guides

In Vivo Use Guide

For oral administration. Adults, the elderly and children 6 years and over: One lozenge dissolved slowly in the mouth every three hours or as required. Do not take more than 12 lozenges in 24 hours. Do not give to children under 6 years.

Route of Administration: Oral

In Vitro Use Guide

TNF-α protein levels were reduced following treatment with Hexylresorcinol at concentrations between 1 and 10μg/mL in RAW264.7 cells.

Name

Type

Language

HEXYLRESORCINOL

Official Name

English

4-Hexylresorcinol

Preferred Name

English

1,3-BENZENEDIOL, 4-HEXYL-

Systematic Name

English

HEXYLRESORCINOL [USP MONOGRAPH]

Common Name

English

HEXYLRESORCINOL [EP MONOGRAPH]

Common Name

English

4-HEXYLRESORCINOL [FCC]

Common Name

English

HEXYLRESORCINOL [USP-RS]

Common Name

English

Hexylresorcinol [WHO-DD]

Common Name

English

INS NO.586

Code

English

4-HEXYL-1,3-BENZENEDIOL

Systematic Name

English

HEXYLRESORCINOL [HSDB]

Common Name

English

HEXYLRESORCINOL [EP IMPURITY]

Common Name

English

4-HEXYLRESORCINOL [MI]

Common Name

English

INS-586

Code

English

HEXYLRESORCINOL [MART.]

Common Name

English

E-586

Code

English

Classification Tree Code System Code

WHO-VATC

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