Showing Compound Phenol (FDB000893)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:45 UTC

Update date

2024-11-29 22:27:43 UTC

Primary ID

FDB000893

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Phenol

Description

Phenol, also known as hydroxybenzene or carbolic acid, belongs to the class of organic compounds known as hydroxy benzenoids. Phenol is a toxic, colourless crystalline solid with a sweet tarry odor that resembles a hospital smell. It is commonly used as an antiseptic and disinfectant. It is active against a wide range of microorganisms including some fungi and viruses but is only slowly effective against spores. It has been used to disinfect skin and to relieve itching. Phenol is also used in the preparation of cosmetics including sunscreens, hair dyes, and skin lightening preparations. It is also used in the production of drugs (it is the starting material in the industrial production of aspirin), weedkillers, and synthetic resins. Phenol can be found in areas with high levels of motor traffic, therefore, people living in crowded urban areas are frequently exposed to traffic-derived phenol vapor. The average (mean +/- SD) phenol concentration in urine among normal individuals living in urban areas is 7.4 +/- 2.2 mg/g of creatinine. Exposure of the skin to concentrated phenol solutions causes chemical burns which may be severe. In laboratories where it is used, it is usually recommended that polyethylene glycol solution is kept available for washing off splashes. In some bacteria phenol can be directly synthesized from tyrosine via the enzyme tyrosine phenol-lyase [EC:4.1.99.2]. It can be produced by Escherichia and Pseudomonas. Phenol has been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821).

CAS Number

108-95-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Acide carbolique	ChEBI
Acide phenique	ChEBI
Benzenol	ChEBI
Carbolic acid	ChEBI
Carbolsaeure	ChEBI
Hydroxybenzene	ChEBI
Karbolsaeure	ChEBI
Oxybenzene	ChEBI
Phenic acid	ChEBI
Phenylic acid	ChEBI
Phenylic alcohol	ChEBI
PHOH	ChEBI
Liquefied phenol	Kegg
Phenol for disinfection	Kegg
Phenol, liquefied	Kegg
Paoscle	Kegg
Carbolate	Generator
Phenate	Generator
Phenylate	Generator
Anbesol	HMDB
Benzophenol	HMDB
Campho-phenique cold sore gel	HMDB
Campho-phenique gel	HMDB
Campho-phenique liquid	HMDB
Carbolic acid liquid	HMDB
Carbolic oil	HMDB
Carbolicum acidum	HMDB
Carbolsaure	HMDB
Cepastat lozenges	HMDB
Cuticura pain relieving ointment	HMDB
Fenol	HMDB
Fenolo	HMDB
Fenosmolin	HMDB
Fenosmoline	HMDB
Hydroxy-benzene	HMDB
IPH	HMDB
IZAL	HMDB
Liquid phenol	HMDB
Liquified phenol	HMDB
Monohydroxy benzene	HMDB
Monohydroxybenzene	HMDB
Monophenol	HMDB
Phenic	HMDB
Phenic alcohol	HMDB
Phenol alcohol	HMDB
Phenol homopolymer	HMDB
Phenol liquid	HMDB
Phenol molten	HMDB
Phenol polymer-bound	HMDB
Phenol solution	HMDB
Phenol synthetic	HMDB
Phenolated water	HMDB
Phenolated water for disinfection	HMDB
Phenole	HMDB
Phenosmolin	HMDB
Synthetic phenol	HMDB
Tea polyphenol	HMDB
Phenol, sodium salt	HMDB
Phenolate sodium	HMDB
Carbol	HMDB
Phenolate, sodium	HMDB
Sodium phenolate	HMDB
FEMA 3223	db_source
Phenyl alcohol	manual
Phenyl hydrate	manual
Phenyl hydroxide	manual

Predicted Properties

Property	Value	Source
Water Solubility	46.6 g/L	ALOGPS
logP	1.39	ALOGPS
logP	1.67	ChemAxon
logS	-0.31	ALOGPS
pKa (Strongest Acidic)	10.02	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	28.04 m³·mol⁻¹	ChemAxon
Polarizability	9.81 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H6O

IUPAC name

phenol

InChI Identifier

InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H

InChI Key

ISWSIDIOOBJBQZ-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC=CC=C1

Average Molecular Weight

94.1112

Monoisotopic Molecular Weight

94.041864814

Classification

Description

Belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-4-unsubstituted benzenoids

Direct Parent

1-hydroxy-4-unsubstituted benzenoids

Alternative Parents

Substituents

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

phenols (CHEBI:15882 )
a phenol (PHENOL )

Ontology

Hypotension

Psychiatric disorders:

Confusion

Ear and labyrinth disorders:

Tinnitus

General disorders and administration site conditions:

Pain

Nervous system disorders:

Headache

Gastrointestinal disorders:

Cardiac disorders:

Cardiovascular disease

Disposition

Source:

Environmental:

Tobacco smoke

Biological:

Microbe:

Escherichia:

Escherichia coli

Pseudomonas:

Pseudomonas putida

Ingestion

Biological location:

Role

Environmental role:

Industrial application:

Food and nutrition

Household products:

Antimicrobial agent:

Disinfectant

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 76.57%; H 6.43%; O 17.00%	DFC
Melting Point	Fp 41°	DFC
Boiling Point	Bp25 90.2°	DFC
Experimental Water Solubility	82.8 mg/mL at 25 oC	SOUTHWORTH,GR & KELLER,JL (1986)
Experimental logP	1.46	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
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)	splash10-00kf-9000000000-40b376f4e58c23369a01	2014-09-20	View Spectrum
GC-MS	Phenol, 1 TMS, GC-MS Spectrum	splash10-0udi-3900000000-97dfa3be718a9ee7ace4	Spectrum
GC-MS	Phenol, non-derivatized, GC-MS Spectrum	splash10-00kf-9000000000-6fb456992902a13931f9	Spectrum
GC-MS	Phenol, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-78c83ab6ff1d3dfdbec6	Spectrum
GC-MS	Phenol, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-89b0c430b8924ee2afde	Spectrum
GC-MS	Phenol, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-fc01d0ad6740cfd70e13	Spectrum
GC-MS	Phenol, non-derivatized, GC-MS Spectrum	splash10-006w-9000000000-c8b41f2899ca8cc9d4bc	Spectrum
GC-MS	Phenol, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-db80d8b605e20595c679	Spectrum
GC-MS	Phenol, non-derivatized, GC-MS Spectrum	splash10-0udi-3900000000-97dfa3be718a9ee7ace4	Spectrum
Predicted GC-MS	Phenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9000000000-c35c89484e2499c62a49	Spectrum
Predicted GC-MS	Phenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0g4i-9300000000-afd565a878ea36c74def	Spectrum
Predicted GC-MS	Phenol, 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, Negative (Annotated)	splash10-0006-9000000000-e67da0571423f0e6b4b8	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0006-9000000000-e0f57b1e970d0d46597e	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0006-9000000000-e67da0571423f0e6b4b8	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-00kf-9000000000-7bfe3b897e928a8f3a2c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positive	splash10-0006-9000000000-78c83ab6ff1d3dfdbec6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive	splash10-0006-9000000000-89b0c430b8924ee2afde	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positive	splash10-0006-9000000000-fc01d0ad6740cfd70e13	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0006-9000000000-ca4fa5905cccbfeab33a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-e3e33defb000b450bb37	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9200000000-d63db79771e5931b258f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-448a4d79ff53d77a8b16	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-2c7201e803e029dd1aef	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-3fb3990dfbfbde2b8d57	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gba-9000000000-d3da8db6579f32d02c6c	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-a74494cda18ab9fb8055	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-a74494cda18ab9fb8055	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-03a61ff7da92cb08edf8	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-c65d4a4eaa8adde2ddb4	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-9000000000-def7a8d52afb63a3cd67	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-f3c795ffc788635ddbf4	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-08485aaf085c13d5129a	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-08485aaf085c13d5129a	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-52b0f93832ef13f17bd2	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	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

BLS38-K:BLS38-K

EAFUS ID

2977

Dr. Duke ID

PHENOL

BIGG ID

Not Available

KNApSAcK ID

C00002664

HET ID

IPH

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

108-95-2

GoodScent ID

rw1009361

SuperScent ID

Not Available

Wikipedia ID

Phenol

Phenol-Explorer Metabolite ID

Not Available

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
Analgesic	35480	An agent that relieves pain by reducing or blocking pain signals in the brain, commonly used to manage acute or chronic pain, inflammation, and fever, with therapeutic applications in surgery, injury, and disease treatment.	DUKE
Anesthetic		A drug that induces a reversible loss of sensation, used to prevent pain and discomfort during medical procedures, surgeries, and diagnostic tests, promoting patient comfort and facilitating treatment.	DUKE
Anti bacterial	33282	An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.	DUKE
Anti-hemorrhoidal	52217	An agent that reduces swelling and inflammation of hemorrhoids, commonly used to relieve symptoms of hemorrhoidal disease, such as itching, pain, and bleeding, and to prevent further complications.	DUKE
Anti hydrocoele		An agent that relieves abnormal fluid accumulation in the scrotum, specifically targeting the processus or tunica vaginalis, to treat hydrocoele conditions, reducing swelling and discomfort.	DUKE
Anti-incontinence	52217	An agent that helps control urinary incontinence by strengthening pelvic muscles, improving bladder function, or reducing urine production, commonly used to manage overactive bladder, stress incontinence, and urge incontinence.	DUKE
Anti monosodium-glutamate		An antidote for MSG poisoning, neutralizing excessive glutamate effects. Biologically, it regulates glutamate levels, mitigating neurotoxicity. Therapeutically, it's used to treat MSG-induced adverse reactions, such as headaches and nausea, and may have applications in managing conditions like migraines and neuropathic pain.	DUKE
Anti onychogryphotic		An agent that treats nail hypertrophy, characterized by overgrowth resembling claws or a ram's horn, by reducing abnormal nail growth. Its therapeutic applications include managing onychogryphosis, a condition often affecting the elderly. Key medical uses include treating deformed or thickened nails, improving nail appearance and function.	DUKE
Anti otitic	52217	An agent that reduces inflammation and infection in the ear, commonly used to treat otitis media (middle ear infection) and other ear disorders, promoting hearing health and alleviating symptoms such as pain and discomfort.	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-prostatitic		An agent that relieves prostatitis, reducing inflammation of the prostate gland, and is used to treat benign prostatic hyperplasia (BPH) and chronic pelvic pain syndrome.	DUKE
Anti pyruvetic		An agent that reduces pyruvate levels, involved in energy metabolism. It has therapeutic applications in managing conditions like cancer, where pyruvate metabolism is altered. Key medical uses include inhibiting tumor growth and improving treatment outcomes in certain cancers.	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-sinusitic		An agent that relieves sinus congestion and pressure, reducing inflammation and discomfort. It is used to treat sinusitis, colds, and allergies, providing therapeutic relief from respiratory symptoms such as congestion, headaches, and facial pain.	DUKE
Anti spastic		An agent that prevents or relieves muscle spasms, used to treat conditions like cerebral palsy, multiple sclerosis, and spinal cord injuries, reducing muscle stiffness and improving mobility.	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
Anti-wrinkle		An agent that prevents or diminishes wrinkle formation, often a factor of aging, used therapeutically to reduce fine lines and skin folds, with key medical applications in cosmetic dermatology and facial rejuvenation.	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
Central nervous system depressant	35470	An agent that slows brain activity, reducing anxiety, stress, and excitability. Therapeutically, it's used to manage insomnia, seizures, and anxiety disorders, promoting relaxation and sedation. Key medical uses include treating insomnia, epilepsy, and panic disorders, as well as inducing anesthesia.	DUKE
Emetic		An agent that induces vomiting, playing a biological role in expelling toxins from the body. Therapeutically, it is used to treat poisoning, overdose, or gastrointestinal obstruction. Key medical uses include managing drug toxicity and aiding in stomach pumping procedures.	DUKE
Fungicide	24127	An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.	DUKE
Hemolytic		An agent that ruptures red blood cells, playing a biological role in breaking down outdated or damaged cells. Therapeutically, it is used to treat conditions like malaria and certain blood disorders. Key medical uses include managing paroxysmal nocturnal hemoglobinuria and other hemolytic diseases, often requiring careful administration to avoid adverse effects.	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
Rodenticide	33288	An agent that kills rodents, acting as a pesticide to control pest populations. Its biological role is to disrupt normal rodent physiology, often targeting the liver or brain. Therapeutically, rodenticides have limited applications, but are used to manage rodent-borne diseases and protect public health. Key medical uses include preventing the spread of diseases like hantavirus and leptospirosis.	DUKE
Vasodilator	35620	An agent that widens blood vessels, reducing blood pressure and increasing blood flow. It plays a biological role in regulating cardiovascular function. Therapeutically, vasodilators are used to treat conditions such as hypertension, angina, and heart failure, improving oxygen delivery and reducing cardiac workload.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Serum paraoxonase/lactonase 3	PON3	Q15166
Serum paraoxonase/arylesterase 1	PON1	P27169
Serum paraoxonase/arylesterase 2	PON2	Q15165
6-phosphogluconolactonase	PGLS	O95336
Glucose-6-phosphate 1-dehydrogenase	G6PD	P11413
Sulfotransferase 1A1	SULT1A1	P50225
Sulfotransferase 1A2	SULT1A2	P50226
Sulfotransferase 1A3/1A4	SULT1A3	P50224
6-phosphogluconate dehydrogenase, decarboxylating	PGD	P52209

Pathways

Name	SMPDB Link	KEGG Link
Metabolism and Physiological Effects of Phenyl sulfate	SMP0123213	Not Available
Metabolism and Physiological Effects of Phenyl glucuronide	SMP0123227	Not Available
Metabolism and Physiological Effects of Phenol	SMP0123255	Not Available
Metabolism and Physiological Effects of Phenol sulphate	SMP0126844	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
phenol	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
phenolic	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
plastic	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
rubber	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.