Showing Compound 1,2-Benzenediol (FDB001512)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:00 UTC

Update date

2019-11-26 02:56:32 UTC

Primary ID

FDB001512

Secondary Accession Numbers

FDB030715
FDB007351

Chemical Information

FooDB Name

1,2-Benzenediol

Description

Pyrocatechol, also known as 1,2-benzenediol or 2-hydroxyphenol, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. Pyrocatechol is an extremely weak basic (essentially neutral) compound (based on its pKa). Pyrocatechol exists in all living organisms, ranging from bacteria to humans. Pyrocatechol is found, on average, in the highest concentration within a few different foods, such as arabica coffee, coffee, and cocoa powders and in a lower concentration in beers. Pyrocatechol has also been detected, but not quantified in, several different foods, such as bamboo shoots, mandarin orange (clementine, tangerine), scarlet beans, naranjilla, and asparagus. This could make pyrocatechol a potential biomarker for the consumption of these foods. Pyrocatechol is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound.

CAS Number

120-80-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,2-Benzenediol	ChEBI
1,2-Dihydroxybenzene	ChEBI
2-Hydroxyphenol	ChEBI
alpha-Hydroxyphenol	ChEBI
Brenzcatechin	ChEBI
O-Benzenediol	ChEBI
O-Hydroxyphenol	ChEBI
Pyrocatechin	ChEBI
a-Hydroxyphenol	Generator
Α-hydroxyphenol	Generator
Catechol	HMDB
Durafur developer C	HMDB
Fouramine PCH	HMDB
Fourrine 68	HMDB
O-Dihydroxybenzene	HMDB
O-Dioxybenzene	HMDB
O-Hydroquinone	HMDB
O-Phenylenediol	HMDB
Oxyphenate	HMDB
Oxyphenic acid	HMDB
Pelagol grey C	HMDB
Phthalhydroquinone	HMDB
Phthalic alcohol	HMDB
Pyrocatechine	HMDB
1,3-Dihydroxybenzene	HMDB
Catechol dipotassium salt	HMDB
Catechol, 14C-labeled CPD	HMDB
Catechol sodium salt	HMDB
Benzene-1,2-diol	PhytoBank
Pyrocatechol	PhytoBank
1,2-Hydroxybenzene	PhytoBank
Catechin (obsol.)?	db_source
Catechol?	db_source
o-Benzenediol	manual
o-Dihydroxybenzene	manual
o-Dioxybenzene	manual
o-Hydroquinone	manual
o-Hydroxyphenol	manual
o-Phenylenediol	manual
Pyrocatechol, 8CI	db_source
α-hydroxyphenol	Generator

Predicted Properties

Property	Value	Source
Water Solubility	75 g/L	ALOGPS
logP	0.74	ALOGPS
logP	1.37	ChemAxon
logS	-0.17	ALOGPS
pKa (Strongest Acidic)	9.34	ChemAxon
pKa (Strongest Basic)	-6.3	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	10.69 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

Chemical Formula

C6H6O2

IUPAC name

benzene-1,2-diol

InChI Identifier

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

InChI Key

YCIMNLLNPGFGHC-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC=CC=C1O

Average Molecular Weight

110.1106

Monoisotopic Molecular Weight

110.036779436

Classification

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
1-hydroxy-4-unsubstituted benzenoid
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

catechols (CHEBI:18135 )
a catechol (CATECHOL )

Ontology

Physiological effect

Health effect:

Health condition:

Schizophrenia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological location:

Role

Indirect biological role:

Genotoxin

Environmental role:

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Foods

Cocoa and cocoa products

Grains:

Cereal products:

Whole grain cereal products

Nuts and legumes:

Fruits and vegetables:

Fats and oils:

Oils:

Vegetable oils:

Olive oil

Beverages:

Coffee products

Alcohols:

Fermented alcohols:

Wine:

Red wine

Infusions:

Tea products

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	105 oC
Boiling Point	Not Available
Experimental Water Solubility	461 mg/mL at 25 oC	YALKOWSKY,SH & HE,Y (2003)
Experimental logP	0.88	HANSCH,C ET AL. (1995)
Experimental pKa	9.45
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-03di-9600000000-b8e03f4f3ea89044828e	2014-09-20	View Spectrum
GC-MS	1,2-Benzenediol, non-derivatized, GC-MS Spectrum	splash10-0udr-1950000000-16187bb35dcb40c26e78	Spectrum
GC-MS	1,2-Benzenediol, non-derivatized, GC-MS Spectrum	splash10-03di-8900000000-4e15f35dca47661de590	Spectrum
GC-MS	1,2-Benzenediol, non-derivatized, GC-MS Spectrum	splash10-03di-9600000000-032a40483dec93738075	Spectrum
GC-MS	1,2-Benzenediol, non-derivatized, GC-MS Spectrum	splash10-03di-7900000000-83f892852c355a3863e9	Spectrum
GC-MS	1,2-Benzenediol, non-derivatized, GC-MS Spectrum	splash10-03di-9400000000-90885264baa17f65d954	Spectrum
GC-MS	1,2-Benzenediol, non-derivatized, GC-MS Spectrum	splash10-0udr-1950000000-16187bb35dcb40c26e78	Spectrum
GC-MS	1,2-Benzenediol, non-derivatized, GC-MS Spectrum	splash10-0udr-1930000000-24d2e0a8e36245d9e187	Spectrum
Predicted GC-MS	1,2-Benzenediol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03di-7900000000-8b112b8af75eb2d08676	Spectrum
Predicted GC-MS	1,2-Benzenediol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fl9-9730000000-a35befff1c602124f29e	Spectrum
Predicted GC-MS	1,2-Benzenediol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2-Benzenediol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2-Benzenediol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2-Benzenediol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1,2-Benzenediol, TBDMS_2_1, 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)	splash10-01ox-9400000000-d59dce8c5e56b026f8b2	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-9000000000-632cabc9b371835019c1	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-02t9-9200000000-ac902cb99981017de3b5	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive	splash10-03di-8900000000-95af3d2738de98d27f26	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-03di-9600000000-032a40483dec93738075	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-03di-7900000000-f5cb1c53768e05ca1530	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0a4i-0900000000-c94dab4d218dbb3bb108	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0a4i-1900000000-edd8ba1e77bbb2f76304	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-0900000000-c94dab4d218dbb3bb108	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-1900000000-edd8ba1e77bbb2f76304	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-0a4i-0900000000-12053747e62e910151ad	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-72e952ea8e487994be54	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-19b1bae28f3dfde3323a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0006-9000000000-33b2a7e7a951547dfafa	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-6e731d4eaba18fcad18f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-1900000000-a7c1a830ea96e82252bf	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-3772b2cca96bf4a1b05f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-9531f3e0c85e67d6c6ed	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1900000000-5886b926a1814092c4b1	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-66523f3122b954e6400f	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1900000000-5fd776e479836f7464af	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-2c46a1375dbb634ef735	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-986c93875cb12d90fa90	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-a301685abb4194689ca3	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9500000000-2017b42835ace86f16ee	2015-05-27	View Spectrum

NMR

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

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Phenol-Explorer ID

DrugBank ID

HMDB ID

CRC / DFC (Dictionary of Food Compounds) ID

HJX14-Z:HJX14-Z

EAFUS ID

Not Available

Dr. Duke ID

PYROCATECHOL|(+)-CATECHOL|CATECHOL

BIGG ID

Not Available

KNApSAcK ID

C00002644

HET ID

CAQ

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Pyrocatechol

Phenol-Explorer Metabolite ID

654

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Allelochemic		A chemical released by plants that interacts with other organisms, influencing their behavior or growth. Its biological role involves plant defense and communication. Therapeutically, allelochemics have anti-inflammatory, antimicrobial, and antioxidant properties, with applications in managing anxiety, pain, and infections, as well as potential anticancer uses.	DUKE
Allergenic	50904	A substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions.	DUKE
Anti-cancer	35610	An agent that inhibits the growth and proliferation of cancer cells, used to treat and manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, to reduce tumor size, prevent metastasis, and improve patient survival.	DUKE
Anti gonadotropic		An agent that suppresses gonadotropin activity, specifically follicle-stimulating hormone (FSH) and luteinizing hormone (LH). Used to treat hormonally-sensitive cancers, delay puberty, and manage conditions like endometriosis and hypersexuality.	DUKE
Anti hepatitic	62868	An agent that protects the liver from damage, reducing inflammation and promoting liver health. Therapeutically, it is used to treat hepatitis and other liver diseases, managing symptoms and preventing liver damage. Key medical uses include treating viral hepatitis, liver cirrhosis, and liver cancer, as well as supporting liver function in patients with liver disease.	DUKE
Anti hepatotoxic	62868	An agent that protects the liver from damage, reducing toxicity and promoting liver health. It plays a biological role in preventing liver injury and supporting liver function. Therapeutically, it is used to treat liver diseases, such as hepatitis and cirrhosis, and to counteract liver-damaging effects of certain medications and toxins.	DUKE
Anti-oxidant	22586	An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.	DUKE
Anti septic	33281	An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.	DUKE
Anti-stomatitic		An agent that relieves inflammation of the mucous membrane of the mouth, reducing oral discomfort and pain. Its biological role is to soothe and protect the mucosa, with therapeutic applications in managing mouth ulcers, oral thrush, and other stomatitis-related conditions. Key medical uses include treating oral inflammation, irritation, and infections.	DUKE
Anti-thiamin		A compound that destroys thiamine, used to study thiamine deficiency, with potential applications in managing thiamine-dependent conditions, and researching beriberi and Wernicke-Korsakoff syndrome.	DUKE
Anti-thyreotropic		An antibody that inhibits thyrotropin, regulating thyroid hormone production. It has therapeutic applications in managing thyroid disorders, such as hyperthyroidism, and key medical uses include treating conditions like Graves' disease.	DUKE
Antitumor	35610	An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.	DUKE
Anti-viral	22587	An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.	DUKE
Cancer preventive	35610	An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.	DUKE
Carcinogenic	50903	An agent that causes cancer, damaging cellular DNA and disrupting normal cell growth. It has no therapeutic applications, but understanding its biological role informs cancer prevention and treatment strategies, with key medical uses in oncology research and risk assessment.	DUKE
Cardiovascular	38070	A system that transports blood, oxygen, and nutrients throughout the body, playing a crucial role in overall health. Therapeutically, cardiovascular agents manage conditions like hypertension, heart failure, and atherosclerosis, with key medical uses including regulating blood pressure, preventing blood clots, and improving cardiac function.	DUKE
Central nervous system stimulant	35470	An agent that increases alertness and activity by enhancing neurotransmitter release, used therapeutically to manage attention deficit hyperactivity disorder (ADHD), narcolepsy, and fatigue, and to improve cognitive function and mood.	DUKE
Convulsant		An agent that induces convulsions and/or epileptic seizures, acting as a stimulant at low doses. It has no therapeutic applications due to its high risk of causing seizures and excitotoxicity, and is the opposite of an anticonvulsant.	DUKE
Dermatitigenic		An agent that causes inflammation of the skin (dermatitis), triggering allergic reactions and immune responses. Its biological role involves activating immune cells, leading to skin irritation. Therapeutically, it is used to test skin sensitivity and develop treatments for dermatitis. Key medical uses include diagnosing skin allergies and researching dermatitis treatments.	DUKE
Dye	37958	A coloring agent with various biological roles, therapeutic applications, and medical uses, including diagnostic imaging, photodynamic therapy, and wound healing, while also serving as a contrast agent to enhance visualization in medical imaging procedures.	DUKE
Fatal		A condition or agent that causes death, having no therapeutic applications or biological role, but is a key consideration in medical fields such as toxicology, emergency medicine, and forensic science, where understanding fatal outcomes is crucial for prevention and treatment of life-threatening conditions.	DUKE
Herbicide	24527	A chemical agent that kills or inhibits plant growth, used in agriculture to control weeds and pests. It has no direct biological role or therapeutic applications in human medicine, but its development has led to the creation of related compounds with potential medical uses, such as anticancer agents.	DUKE
Insectifuge	24852	A substance that repels insects, playing a biological role in plant defense. Therapeutically, it has applications in preventing insect-borne diseases. Key medical uses include topical repellents for malaria, dengue fever, and other vector-borne illnesses, reducing the risk of transmission.	DUKE
Nematicide	25491	An agent that kills nematodes, a type of parasitic worm, used to control infestations in crops and animals, with therapeutic applications in veterinary medicine to treat parasitic infections and promote livestock health.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Quinone-reductase inducer		An agent that stimulates quinone reductase enzymatic activity, enhancing cellular antioxidant defenses and protecting against carcinogens, with therapeutic applications in cancer chemoprevention and potential uses in managing oxidative stress-related diseases.	DUKE
Tumor promoter	50903	A substance that enhances the growth and proliferation of cancer cells, often used in research to study cancer development. Therapeutically, understanding tumor promoters informs cancer prevention and treatment strategies, with applications in oncology for developing targeted therapies to inhibit tumor growth and progression.	DUKE
Genotoxic	50902	An agent that damages genetic material, disrupting DNA structure and function. It has a biological role in inducing mutations and cancer. Therapeutically, genotoxic agents are used in chemotherapy to target rapidly dividing cancer cells. Key medical uses include cancer treatment, with applications in oncology for killing malignant cells and inhibiting tumor growth.	CHEBI