Record Information
Version1.0
Creation date2010-04-08 22:10:57 UTC
Update date2020-09-17 15:39:53 UTC
Primary IDFDB013879
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhloroglucinol
Description1,3,5-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 Number108-73-6
Structure
Thumb
Synonyms
SynonymSource
1,3,5-BenzenetriolChEBI
Benzene-1,3,5-triolChEBI
S-TrihydroxybenzeneChEBI
Dilospan SKegg
1,3, 5-TrihydroxybenzeneHMDB
1,3,5-Benzenetriol (acd/name 4.0)HMDB
1,3,5-Trihydroxy-benzeneHMDB
1,3,5-TrihydroxycyclohexatrieneHMDB
1,3,5-TriolHMDB
3,5-DihydroxyphenolHMDB
5-BenzenetriolHMDB
5-HydroxyresorcinolHMDB
5-OxyresorcinolHMDB
5-OxyresorcinolphloroglucinHMDB
Benzene, trihydroxyHMDB
Benzene-S-triolHMDB
FloroglucinHMDB
FloroglucinolHMDB
PhloroglucinHMDB
PhloroglucineHMDB
Phloroglucinol (1,3,5-benzenetriol)HMDB
Spasfon-lyocHMDB
Sym-trihydroxybenzeneHMDB
1,3,5-TrihydroxybenzeneChEBI
SpassirexMeSH
PhloroglucinolHMDB
Spasfon-Lyocdb_source
Predicted Properties
PropertyValueSource
Water Solubility35.8 g/LALOGPS
logP0.25ALOGPS
logP1.06ChemAxon
logS-0.55ALOGPS
pKa (Strongest Acidic)9.13ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity32 m³·mol⁻¹ChemAxon
Polarizability11.69 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H6O3
IUPAC namebenzene-1,3,5-triol
InChI IdentifierInChI=1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H
InChI KeyQCDYQQDYXPDABM-UHFFFAOYSA-N
Isomeric SMILESOC1=CC(O)=CC(O)=C1
Average Molecular Weight126.11
Monoisotopic Molecular Weight126.031694058
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenetriols and derivatives
Direct ParentPhloroglucinols 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 57.14%; H 4.80%; O 38.06%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSPhloroglucinol, non-derivatized, GC-MS Spectrumsplash10-0037-1925000000-c724191b9103115057caSpectrum
GC-MSPhloroglucinol, non-derivatized, GC-MS Spectrumsplash10-0037-1925000000-c724191b9103115057caSpectrum
Predicted GC-MSPhloroglucinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-1900000000-dd0ed35d23318896d1b9Spectrum
Predicted GC-MSPhloroglucinol, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-9266000000-2317d43ce1d2bdb60083Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-9000000000-104015e2f367513be83dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-000o-9000000000-66ca2cf660ad4426c021Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-1900000000-d25737e313306ff2b48dSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004i-1900000000-6a0b9a2f7d646e89cea4Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-004i-3900000000-d102992a3cf4a244a8c6Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-004i-7900000000-e4022d17507410f9dea6Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-0a6r-9500000000-efa09c9675e92917dc71Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-0a4i-9200000000-b8189deed5b441103a17Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-0a4i-9100000000-91c096b5c6bca93fb201Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, negativesplash10-0a4i-9000000000-2dfdf462ad4af57dd4eeSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-0a4i-9000000000-0e5ee4e7603fdee5aa91Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, negativesplash10-0a4i-9000000000-ee965d165837c624e0a4Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-0a4i-9000000000-42a5aadbd8a2700fcb8aSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-0a4i-9000000000-ced455fb5a135cb19c2eSpectrum
MS/MSLC-MS/MS Spectrum - n/a 8V, negativesplash10-001i-9000000000-23bf2d29b2666f3f65faSpectrum
MS/MSLC-MS/MS Spectrum - QTOF 3V, positivesplash10-004i-0900000000-4e75317d3710eb5b0c50Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-004i-0900000000-944db6cc318783777622Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-004i-0900000000-c9f3189fb88bc03828f1Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-004i-0900000000-11900ad61e01b6d4449bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-85c95c94bd781f89f712Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-75dcf760031bb09416a1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2900000000-8f7164ec36db279bbbbfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-09436c8cdb204e5cecb4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-46ba64f6b6c946b31aaeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-6900000000-776dffab62c69a4b4b02Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID658
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJJJ54-P:JJJ54-P
EAFUS IDNot Available
Dr. Duke ID1,3,5-TRIHYDROXY-BENZENE|PHLOROGLUCINOL
BIGG IDNot Available
KNApSAcK IDC00002665
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
antitumor promoter35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
decalcifierDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
goitrogenicDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
prostaglandin synthesis inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.