Cannabis Compound Database: Showing Compound Card for Hydroquinone (CDB005110)

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (7)transporters (1) Show 11 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 19:10:18 UTC

Updated at

2021-01-04 18:48:58 UTC

CannabisDB ID

CDB005110

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Hydroquinone

Description

Hydroquinone, also known as quinol or eldoquin, belongs to the class of organic compounds known as hydroquinones. Hydroquinones are compounds containing a hydroquinone moiety, which consists of a benzene ring with a hydroxyl groups at positions 1 and 4 (the para-positions). Hydroquinone is also classified as a phenol. It exists as a white granular solid and is moderately soluble in water. Hydroquinone is produced industrially and used as a water-soluble reducing agent or anti-oxidant. It is a major component in most black and white photographic developer solutions for film and paper where, with the compound metol, it reduces silver halides to elemental silver. Hydroquinone is also widely used as a polymerization inhibitor to prevent radical-initiated polymerization of acrylic acid or methyl acrylate. It is also used as a stabilizing agent in several cosmetics. Medically, hydroquinone has been formulated into creams, lotions and gels as a topical application to whiten skin and reduce skin hyperpigmentation. Over-the-counter sales of creams containing hydroquinone have been limited as it is a potential carcinogen. As a result of these concerns, hydroquinone has been banned in the EU and UK. However, it is still widely used in prescription medications to correct skin discoloration associated with disorders of hyperpigmentation including melasma, post-inflammatory hyperpigmention, sunspots, and freckles. Numerous studies have revealed that hydroquinone can cause exogenous ochronosis, a disfiguring disease in which blue-black pigments are deposited onto the skin, if taken orally; however, skin preparations containing the ingredient are administered topically. Hydroquinone exists in all living organisms, ranging from bacteria to plants to humans. The presence of hydroquinone in normal individuals stems mainly from direct dietary ingestion, catabolism of tyrosine and other substrates by gut bacteria, ingestion of arbutin containing foods, cigarette smoking, and the use of some over-the-counter medicines. Hydroquinone is produced naturally by plants and has been detected in many different plants and plant foods including sweet oranges, anise, bilberries, lingonberries, pears, skunk currants, sesbania flowers, japanese chestnuts, and bamboo shoots. This could make hydroquinone a potential biomarker for the consumption of these foods. Hydroquinone is one of several phenolic compounds found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1,4-Benzenediol	ChEBI
1,4-Dihydroxybenzene	ChEBI
4-Hydroxyphenol	ChEBI
Benzene-1,4-diol	ChEBI
Eldoquin	ChEBI
p-Benzenediol	ChEBI
p-Hydroquinone	ChEBI
p-Hydroxyphenol	ChEBI
Quinol	ChEBI
Artra	MeSH
Eldopaque	MeSH
Esoterica	MeSH
Hidroquilaude	MeSH
Hidroquin	MeSH
Hidroquinona isdin	MeSH
Licostrata	MeSH
Lustra	MeSH
Melanasa	MeSH
Melanex	MeSH
Melpaque	MeSH
Melquin	MeSH
Neostrata HQ	MeSH
Phiaquin	MeSH
Solaquin	MeSH
Ultraquin	MeSH
beta-Quinol	MeSH
Hydroquinone, copper (1+) salt	MeSH
Hydroquinone, lead (2+) salt (2:1)	MeSH
Hydroquinone, monocopper (2+) salt	MeSH
1,4-Dihydroxy-benzeen	HMDB
1,4-Dihydroxy-benzol	HMDB
1,4-Dihydroxybenzen	HMDB
1,4-Diidrobenzene	HMDB
a-Hydroquinone	HMDB
alpha-Hydroquinone	HMDB
b-Quinol	HMDB
Benzohydroquinone	HMDB
Benzoquinol	HMDB
Dihydroquinone	HMDB
Dihydroxybenzene	HMDB
Hydrochinon	HMDB
Hydrochinone	HMDB
Hydroquinol	HMDB
Hydroquinole	HMDB
Hydroquinone for synthesis	HMDB
Hydroquinone GR	HMDB
Hydroquinoue	HMDB
Idrochinone	HMDB
p-Dihydroxybenzene	HMDB
P-Dioxobenzene	HMDB
p-Dioxybenzene	HMDB
P-Hydroxybenzene	HMDB
Solaquin forte	HMDB
Eldoquin forte	MeSH, HMDB
Stratus brand 1 OF hydroquinone	MeSH, HMDB
ICN brand 1 OF hydroquinone	MeSH, HMDB
Plough brand 2 OF hydroquinone	MeSH, HMDB
Eldopaque forte	MeSH, HMDB
ICN brand 4 OF hydroquinone	MeSH, HMDB
Black and white	MeSH, HMDB
ICN brand 2 OF hydroquinone	MeSH, HMDB
ICN brand 3 OF hydroquinone	MeSH, HMDB
Plough brand 1 OF hydroquinone	MeSH, HMDB
Stratus brand 2 OF hydroquinone	MeSH, HMDB
1,4-Benzoquinol	PhytoBank
1,4-Phenylenediol	PhytoBank
1,4-p-Benzenediol	PhytoBank
p-Dihydroquinone	PhytoBank
p-Phenylenediol	PhytoBank
p-Quinol	PhytoBank

Chemical Formula

C₆H₆O₂

Average Molecular Weight

110.11

Monoisotopic Molecular Weight

110.0368

IUPAC Name

benzene-1,4-diol

Traditional Name

α-hydroquinone

CAS Registry Number

123-31-9

SMILES

OC1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8H

InChI Key

QIGBRXMKCJKVMJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroquinones. Hydroquinones are compounds containing a hydroquinone moiety, which consists of a benzene ring with a hydroxyl groups at positions 1 and 4.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Hydroquinone
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

hydroquinones (CHEBI:17594 )
benzenediol (CHEBI:17594 )
an electron-transfer-related quinol (HYDROQUINONE )
a benzenediol (HYDROQUINONE )

Ontology

Physiological effect

Health effect:

Health condition:

Uremia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Synthetic:

Personal care product

Environmental:

Tobacco smoke

Biological:

Animal

Plant:

Biological location:

Tissue and substructures:

Epidermis

Cell and elements:

Cell:

Fibroblast

Organ and components:

Biofluid and excreta:

Subcellular:

Role

Indirect biological role:

Carcinogen

Environmental role:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	172.3 °C	Not Available
Boiling Point	287 °C	Wikipedia
Water Solubility	72 mg/mL at 25 °C	Not Available
logP	0.59	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	0.71	ALOGPS
logP	1.37	ChemAxon
logS	-0.06	ALOGPS
pKa (Strongest Acidic)	9.68	ChemAxon
pKa (Strongest Basic)	-5.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	30.02 m³·mol⁻¹	ChemAxon
Polarizability	10.75 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-03di-9500000000-1fa8477944a662535e76	2014-09-20	View Spectrum
GC-MS	Hydroquinone, 2 TMS, GC-MS Spectrum	splash10-0f79-2490000000-6b4fec222a3499d93790	Spectrum
GC-MS	Hydroquinone, non-derivatized, GC-MS Spectrum	splash10-03di-9800000000-c90fd4986fea9691ecbf	Spectrum
GC-MS	Hydroquinone, non-derivatized, GC-MS Spectrum	splash10-03e9-9300000000-f8b11742557329691e8a	Spectrum
GC-MS	Hydroquinone, non-derivatized, GC-MS Spectrum	splash10-0f79-2490000000-6b4fec222a3499d93790	Spectrum
GC-MS	Hydroquinone, non-derivatized, GC-MS Spectrum	splash10-0f79-2690000000-7306adcc7121a11d67cc	Spectrum
Predicted GC-MS	Hydroquinone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03di-5900000000-954dc96d8e3eb85b8324	Spectrum
Predicted GC-MS	Hydroquinone, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00e9-8950000000-512c0cf5ddc0b120ec8e	Spectrum
Predicted GC-MS	Hydroquinone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Hydroquinone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-9600000000-e670ba090cb27367db12	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-01p6-9000000000-5fc32c7688c1612df1e7	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9000000000-c5853ce8ef225ea5c353	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-03di-9800000000-c90fd4986fea9691ecbf	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-0a4i-0900000000-5635f0157cd37deb1121	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-03di-2900000000-05be113033a709130eed	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9600000000-e0d15b2e4ea35a7a76be	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-01r6-9000000000-946504408977df40269a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-c16180dd26c127563155	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9000000000-cea1cb486f12ea31e3a1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-01ox-9000000000-3a9d5710c88793e698f1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-60eeaa79bff371773b2e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-3a9e293da186985db7fa	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0pb9-9000000000-84bb0a9b4c3cd16da2a7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-7900000000-2256214c81a3e04e01b7	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-8d8328e4f7cd2ebaa27d	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1900000000-9290fcb93f170fc3143f	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01si-9200000000-9f707b9d0c4ad0b73b30	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-d3aae38632ac4c40fd4f	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-74f15490ba4f49cf8c18	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9800000000-1cb01248e88fce387578	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-9f2c82efe2cba7470e17	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-9f2c82efe2cba7470e17	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f6x-9000000000-8213c13cc381b346f976	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-fd10fd64675560620b8d	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.08 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Riboflavin Metabolism
Glycerolipid Metabolism
Glycerol Kinase Deficiency		Not Available
D-glyceric acidura		Not Available
Familial lipoprotein lipase deficiency		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Tyrosinase	TYR	11q14-q21	P14679	details
Serum paraoxonase/lactonase 3	PON3	7q21.3	Q15166	details
Serum paraoxonase/arylesterase 1	PON1	7q21.3	P27169	details
Serum paraoxonase/arylesterase 2	PON2	7q21.3	Q15165	details
Ribosyldihydronicotinamide dehydrogenase [quinone]	NQO2	6p25.2	P16083	details
UDP-glucuronosyltransferase 1-1	UGT1A1	2q37	P22309	details
NAD(P)H dehydrogenase [quinone] 1	NQO1	16q22.1	P15559	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Serum paraoxonase/arylesterase 1	PON1	7q21.3	P27169	details

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Serum paraoxonase/lactonase 3	PON3	7q21.3	Q15166	details
Serum paraoxonase/arylesterase 2	PON2	7q21.3	Q15165	details
Ribosyldihydronicotinamide dehydrogenase [quinone]	NQO2	6p25.2	P16083	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0002434

DrugBank ID

DB09526

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Hydroquinone

METLIN ID

6681

PubChem Compound

785

PDB ID

Not Available

ChEBI ID

17594

References

General References

Not Available

Only showing the first 10 proteins. There are 11 proteins in total.

Show All

Enzymes

Enzyme Details

1. Tyrosinase

General function:: Involved in oxidoreductase activity
Specific function:: This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the rate-limiting conversions of tyrosine to DOPA, DOPA to DOPA-quinone and possibly 5,6-dihydroxyindole to indole-5,6 quinone.
Gene Name:: TYR
Uniprot ID:: P14679
Molecular weight:: 60392.69

Enzyme Details

2. Serum paraoxonase/lactonase 3

General function:: Involved in arylesterase activity
Specific function:: Has low activity towards the organophosphate paraxon and aromatic carboxylic acid esters. Rapidly hydrolyzes lactones such as statin prodrugs (e.g. lovastatin). Hydrolyzes aromatic lactones and 5- or 6-member ring lactones with aliphatic substituents but not simple lactones or those with polar substituents.
Gene Name:: PON3
Uniprot ID:: Q15166
Molecular weight:: 39607.185

Enzyme Details

3. Serum paraoxonase/arylesterase 1

General function:: Involved in arylesterase activity
Specific function:: Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxylic acid esters. Mediates an enzymatic protection of low density lipoproteins against oxidative modification and the consequent series of events leading to atheroma formation.
Gene Name:: PON1
Uniprot ID:: P27169
Molecular weight:: 39730.99

Enzyme Details

4. Serum paraoxonase/arylesterase 2

General function:: Involved in arylesterase activity
Specific function:: Capable of hydrolyzing lactones and a number of aromatic carboxylic acid esters. Has antioxidant activity. Is not associated with high density lipoprotein. Prevents LDL lipid peroxidation, reverses the oxidation of mildly oxidized LDL, and inhibits the ability of MM-LDL to induce monocyte chemotaxis.
Gene Name:: PON2
Uniprot ID:: Q15165
Molecular weight:: 39380.535

Enzyme Details

5. Ribosyldihydronicotinamide dehydrogenase [quinone]

General function:: Involved in electron carrier activity
Specific function:: The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:: NQO2
Uniprot ID:: P16083
Molecular weight:: 25918.4

Enzyme Details

6. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Enzyme Details

7. NAD(P)H dehydrogenase [quinone] 1

General function:: Involved in electron carrier activity
Specific function:: The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinons involved in detoxification pathways as well as in biosynthetic processes such as the vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:: NQO1
Uniprot ID:: P15559
Molecular weight:: 30867.405

Transporters

Enzyme Details

1. Serum paraoxonase/arylesterase 1

General function:: Involved in arylesterase activity
Specific function:: Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxylic acid esters. Mediates an enzymatic protection of low density lipoproteins against oxidative modification and the consequent series of events leading to atheroma formation.
Gene Name:: PON1
Uniprot ID:: P27169
Molecular weight:: 39730.99

Only showing the first 10 proteins. There are 11 proteins in total.

Show All

Showing Compound Card for Hydroquinone (CDB005110)

Structure for CDB005110 (Hydroquinone)

Enzymes

Transporters