Showing Compound Phloroglucinol (FDB013879)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:57 UTC

Update date

2025-11-19 00:37:54 UTC

Primary ID

FDB013879

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Phloroglucinol

Description

1,3,5-Trihydroxybenzene, also known as 1,3,5-benzenetriol or benzene-1,3,5-triol, belongs to the class of organic compounds known as phloroglucinols and derivatives. Phloroglucinols and derivatives are compounds containing a phloroglucinol (benzene-1,3,5-triol) moiety, which consists of a benzene ring bearing one hydroxyl group at positions 1,3, and 5. It is an organic compound that is used in the synthesis of pharmaceuticals and explosives. This molecule exists in two forms, or tautomers, 1,3,5-trihydroxybenzene, which has phenol-like, and 1,3,5-cyclohexanetrione (phloroglucin), which has ketone-like character. 1,3,5-Trihydroxybenzene has been found to be a metabolite in Pseudomonas (PMID: 15826166). 1,3,5-Trihydroxybenzene is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 1,3,5-Trihydroxybenzene is found, on average, in the highest concentration within garden onions. 1,3,5-Trihydroxybenzene has also been detected, but not quantified in, several different foods, such as carobs, highbush blueberries, soft-necked garlics, tarragons, and tea. This could make 1,3,5-trihydroxybenzene a potential biomarker for the consumption of these foods. These two tautomers are in equilibrium. Phloroglucinol is a useful intermediate because it is polyfunctional. Phloroglucinol is a benzenetriol.

CAS Number

108-73-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,3,5-Benzenetriol	ChEBI
Benzene-1,3,5-triol	ChEBI
S-Trihydroxybenzene	ChEBI
Dilospan S	Kegg
1,3,5-Trihydroxybenzene	ChEBI
1,3, 5-Trihydroxybenzene	HMDB
1,3,5-Benzenetriol (acd/name 4.0)	HMDB
1,3,5-Trihydroxy-benzene	HMDB
1,3,5-Trihydroxycyclohexatriene	HMDB
1,3,5-Triol	HMDB
3,5-Dihydroxyphenol	HMDB
5-Benzenetriol	HMDB
5-Hydroxyresorcinol	HMDB
5-Oxyresorcinol	HMDB
5-Oxyresorcinolphloroglucin	HMDB
Benzene, trihydroxy	HMDB
Benzene-S-triol	HMDB
Floroglucin	HMDB
Floroglucinol	HMDB
Phloroglucin	HMDB
Phloroglucine	HMDB
Phloroglucinol (1,3,5-benzenetriol)	HMDB
Spasfon-lyoc	HMDB, MeSH
Sym-trihydroxybenzene	HMDB
Spassirex	MeSH
Phloroglucinol	HMDB
Spasfon-Lyoc	db_source

Predicted Properties

Property	Value	Source
Water Solubility	35.8 g/L	ALOGPS
logP	0.25	ALOGPS
logP	1.06	ChemAxon
logS	-0.55	ALOGPS
pKa (Strongest Acidic)	9.13	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	32 m³·mol⁻¹	ChemAxon
Polarizability	11.69 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

C6H6O3

IUPAC name

benzene-1,3,5-triol

InChI Identifier

InChI=1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H

InChI Key

QCDYQQDYXPDABM-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC(O)=CC(O)=C1

Average Molecular Weight

126.11

Monoisotopic Molecular Weight

126.031694058

Classification

Description

Belongs to the class of organic compounds known as phloroglucinols and derivatives. Phloroglucinols and derivatives are compounds containing a phloroglucinol (benzene-1,3,5-triol) moiety, which consists of a benzene ring bearing one hydroxyl group at positions 1,3, and 5.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

Benzenetriols and derivatives

Direct Parent

Phloroglucinols and derivatives

Alternative Parents

Substituents

Phloroglucinol derivative
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzenetriol (CHEBI:16204 )
a small molecule (CPD-16 )

Ontology

Disposition

Biological location:

Biofluid and excreta:

Feces

Source:

Endogenous

Biological:

Microbe:

Pseudomonas:

Pseudomonas fluorescens

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 57.14%; H 4.80%; O 38.06%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
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
GC-MS	Phloroglucinol, non-derivatized, GC-MS Spectrum	splash10-0037-1925000000-c724191b9103115057ca	Spectrum
GC-MS	Phloroglucinol, non-derivatized, GC-MS Spectrum	splash10-0037-1925000000-c724191b9103115057ca	Spectrum
Predicted GC-MS	Phloroglucinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-1900000000-dd0ed35d23318896d1b9	Spectrum
Predicted GC-MS	Phloroglucinol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9266000000-2317d43ce1d2bdb60083	Spectrum
Predicted GC-MS	Phloroglucinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phloroglucinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-9000000000-104015e2f367513be83d	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, positive	splash10-000o-9000000000-66ca2cf660ad4426c021	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a4i-1900000000-d25737e313306ff2b48d	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-004i-1900000000-6a0b9a2f7d646e89cea4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-004i-3900000000-d102992a3cf4a244a8c6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-004i-7900000000-e4022d17507410f9dea6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-0a6r-9500000000-efa09c9675e92917dc71	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-0a4i-9200000000-b8189deed5b441103a17	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-0a4i-9100000000-91c096b5c6bca93fb201	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-0a4i-9000000000-2dfdf462ad4af57dd4ee	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, negative	splash10-0a4i-9000000000-0e5ee4e7603fdee5aa91	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, negative	splash10-0a4i-9000000000-ee965d165837c624e0a4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, negative	splash10-0a4i-9000000000-42a5aadbd8a2700fcb8a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, negative	splash10-0a4i-9000000000-ced455fb5a135cb19c2e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 8V, negative	splash10-001i-9000000000-23bf2d29b2666f3f65fa	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 3V, positive	splash10-004i-0900000000-4e75317d3710eb5b0c50	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-004i-0900000000-944db6cc318783777622	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-004i-0900000000-c9f3189fb88bc03828f1	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-004i-0900000000-11900ad61e01b6d4449b	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-85c95c94bd781f89f712	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-75dcf760031bb09416a1	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-2900000000-8f7164ec36db279bbbbf	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-09436c8cdb204e5cecb4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-46ba64f6b6c946b31aae	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-6900000000-776dffab62c69a4b4b02	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

658

DrugBank ID

Not Available

HMDB ID

HMDB0013675

CRC / DFC (Dictionary of Food Compounds) ID

JJJ54-P:JJJ54-P

EAFUS ID

Not Available

Dr. Duke ID

1,3,5-TRIHYDROXY-BENZENE|PHLOROGLUCINOL

BIGG ID

Not Available

KNApSAcK ID

C00002665

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Phloroglucinol

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
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-spasmodic	52217	An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.	DUKE
Antitumor promoter	35610	An agent that inhibits tumor growth and progression, reducing cancer cell proliferation. Therapeutically, it prevents tumor development and spread, with key medical uses in cancer prevention and treatment, particularly in combating carcinogenesis and metastasis.	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
Decalcifier		An agent that removes calcium or calcium compounds from targets like bones or teeth, playing a biological role in bone remodeling. Therapeutically, it's used to treat conditions like dental calculus or bone diseases, and has medical applications in orthopedics, dentistry, and histology to prepare specimens for analysis.	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
Goitrogenic		A substance that interferes with thyroid hormone production by blocking iodine uptake, leading to increased TSH release and potential goiter formation, with therapeutic applications in managing hyperthyroidism and certain thyroid disorders.	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
Prostaglandin synthesis inhibitor	35222	An agent that blocks the production of prostaglandins, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and fever, commonly found in nonsteroidal anti-inflammatory drugs (NSAIDs).	DUKE