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Record Information
Version2.0
Creation Date2014-08-29 04:48:33 UTC
Update Date2014-12-24 20:26:35 UTC
Accession NumberT3D3981
Identification
Common Name2-Biphenylol
ClassSmall Molecule
Description2-Biphenylol is found in lemon. It is an antifungal agent and preservative. 2-Biphenylol is used for post-harvest control of storage disease in apples, citrus fruit, stone fruit, tomatoes, cucumber and peppers through the use of impregnated wrapping materials or by direct application in a wax. 2-Biphenylol is used in food seasonings. Inhibitory to a wider range of moulds than Biphenyl HMJ12-A. The practical way of treatment is to immerse citrus fruit in an alkaline aqueous solution of the parent compound or its Na salt. 2-Biphenylol belongs to the family of Biphenyls and Derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
Compound Type
  • Food Additive
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
  • Preservative
Chemical Structure
Thumb
Synonyms
Synonym
(1,1'-Biphenyl)-2-ol
(1,1-Biphenyl)-2-ol
1,1'-Biphenyl-2-ol
1-Hydroxy-2-phenylbenzene
2-Fenylfenol
2-Hydroxy biphenyl
2-Hydroxy-1,1'-biphenyl
2-Hydroxybiphenyl
2-Hydroxydiphenyl
2-Phenylphenol, BSI, ISO
Biphenylol
Dowicide 1
E231
FEMA 3959
HBP
Hydroxdiphenyl
Hydroxy-2-phenylbenzene
Hydroxybiphenyl
Manusept
Nectryl
Nipacide OPP
O-Biphenylol
O-Diphenylol
O-Hydroxybiphenyl
O-Hydroxydiphenyl
O-Phenyl phenol
O-Phenylphenate
O-Phenylphenol
O-Xenol
O-Xonal
OPP?
Ortho-phenylphenate
Ortho-phenylphenol
Orthohydroxydipbenyl
Orthohydroxydiphenyl
Orthophenylphenol
Orthoxenol
Phenylphenol
Rotoline
Stellisept
Torsite
Chemical FormulaC12H10O
Average Molecular Mass170.207 g/mol
Monoisotopic Mass170.073 g/mol
CAS Registry Number90-43-7
IUPAC Name[1,1'-biphenyl]-2-ol
Traditional Nameo-phenylphenol
SMILESOC1=CC=CC=C1C1=CC=CC=C1
InChI IdentifierInChI=1S/C12H10O/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9,13H
InChI KeyInChIKey=LLEMOWNGBBNAJR-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBiphenyls and derivatives
Direct ParentBiphenyls and derivatives
Alternative Parents
Substituents
  • Biphenyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point56°C
Boiling PointNot Available
Solubility0.7 mg/mL at 25°C
LogP3.09
Predicted Properties
PropertyValueSource
Water Solubility0.34 g/LALOGPS
logP3.21ALOGPS
logP3.32ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)9.69ChemAxon
pKa (Strongest Basic)-5.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity53.18 m³·mol⁻¹ChemAxon
Polarizability18.75 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-1900000000-f58c83912c81582962ecJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00xr-1900000000-ba4f084280aee3b63cb9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00xr-2900000000-0395543c94def63fbf1cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03fr-1790000000-2fec91e9a3b831e4f661JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-1900000000-f58c83912c81582962ecJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00xr-1900000000-ba4f084280aee3b63cb9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00xr-2900000000-0395543c94def63fbf1cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03fr-1790000000-2fec91e9a3b831e4f661JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0900000000-43bf1dee532a54447f41JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9760000000-5e1078b290b37f1d47bcJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0fml-0900000000-7b06dbf8c12560a092e6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0fb9-0900000000-dc2a630f122797c0a30dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udl-0900000000-0058244c148d04bcffb9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udl-0900000000-28f041bf0b0faf02ccd5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-aa09c65297232074b1daJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-042a540d9a28eba4bb1eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f96-9600000000-ee2a147f3a7a3bbc0bdaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-05ec524c3078c379ec6fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1900000000-cf114607f489ee954397JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9500000000-075a7f587e50b80d93c6JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-01bc-3900000000-adae00e9be0477f3901bJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (16)
Uses/Sources2-Biphenylol is found in lemon. It is an antifungal agent and preservative. 2-Biphenylol is used for post-harvest control of storage disease in apples, citrus fruit, stone fruit, tomatoes, cucumber and peppers through the use of impregnated wrapping materials or by direct application in a wax. 2-Biphenylol is used in food seasonings. The practical way of treatment is to immerse citrus fruit in an alkaline aqueous solution of the parent compound or its Na salt.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB32582
PubChem Compound ID7017
ChEMBL IDCHEMBL108829
ChemSpider ID13839012
KEGG IDC02499
UniProt IDNot Available
OMIM ID
ChEBI ID17043
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D3981.pdf
General References
  1. Shen DT, Crawford TB, Gorham JR, McGuire TC: Inactivation of equine infectious anemia virus by chemical disinfectants. Am J Vet Res. 1977 Aug;38(8):1217-9. [199094 ]
  2. Johnson GD, Harsy SG, Geronimo J, Wise JM: Orthophenylphenol and phenylhydroquinone residues in citrus fruit and processed citrus products after postharvest fungicidal treatments with sodium orthophenylphenate in California and Florida. J Agric Food Chem. 2001 May;49(5):2497-502. [11368626 ]
  3. Humphreys MJ, Allman R, Lloyd D: Determination of the viability of Trichomonas vaginalis using flow cytometry. Cytometry. 1994 Apr 1;15(4):343-8. [8026224 ]
  4. HOPKINS EF, LOUCKS KW: Prevention of the phytotoxic action of sodium orthophenylphenate on citrus fruits by hexamine. Science. 1950 Dec 15;112(2920):720-1. [14787507 ]
  5. Diaz Borras A, Vila Aguilar R, Hernandez Gimenez E: Synergistic effect of fungicides on resistant strains of Penicillium italicum and Penicillium digitatum. Int J Food Microbiol. 1988 Aug;7(1):79-85. [3275313 ]
  6. Csermely P, Balint E, Grimley PM, Aszalos A: Protein kinase C is involved in the early signals of interferon-alpha but not of interferon-gamma in U937 cells. J Interferon Res. 1990 Dec;10(6):605-11. [2128303 ]
  7. Reitz RH, Fox TR, Quast JF, Hermann EA, Watanabe PG: Biochemical factors involved in the effects of orthophenylphenol (OPP) and sodium orthophenylphenate (SOPP) on the urinary tract of male F344 rats. Toxicol Appl Pharmacol. 1984 Apr;73(2):345-9. [6710533 ]
  8. Cinelli AR, Salzberg BM: Dendritic origin of late events in optical recordings from salamander olfactory bulb. J Neurophysiol. 1992 Sep;68(3):786-806. [1432048 ]
  9. Evans JA, Darlington DN, Gann DS: A circulating factor(s) mediates cell depolarization in hemorrhagic shock. Ann Surg. 1991 Jun;213(6):549-56; discussion 556-7. [2039285 ]
  10. Fangstrom B, Hovander L, Bignert A, Athanassiadis I, Linderholm L, Grandjean P, Weihe P, Bergman A: Concentrations of polybrominated diphenyl ethers, polychlonnated biphenyls, and polychlorobiphenylols in serum from pregnant Faroese women and their children 7 years later. Environ Sci Technol. 2005 Dec 15;39(24):9457-63. [16475322 ]
  11. McDONOUGH ES: Inhibition of mold contamination in Drosophila food using sodium orthophenylphenate. Science. 1953 Oct 2;118(3066):388. [13101762 ]
  12. Santhamma KR, Bhaduri A: Characterization of the respiratory chain of Leishmania donovani promastigotes. Mol Biochem Parasitol. 1995 Dec;75(1):43-53. [8720174 ]
  13. Calori-Domingues MA, Fonseca H: Laboratory evaluation of chemical control of aflatoxin production in unshelled peanuts (Arachis hypogaea L.). Food Addit Contam. 1995 May-Jun;12(3):347-50. [7664926 ]
  14. Ranzani MR, Fonseca H: Mycological evaluation of chemically-treated unshelled peanuts. Food Addit Contam. 1995 May-Jun;12(3):343-6. [7664925 ]
  15. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  16. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Protein kinase binding
Specific Function:
Potent inhibitor of cell death. Inhibits activation of caspases. Appears to regulate cell death by blocking the voltage-dependent anion channel (VDAC) by binding to it and preventing the release of the caspase activator, CYC1, from the mitochondrial membrane. Also acts as a regulator of G2 checkpoint and progression to cytokinesis during mitosis.Isoform Bcl-X(L) also regulates presynaptic plasticity, including neurotransmitter release and recovery, number of axonal mitochondria as well as size and number of synaptic vesicle clusters. During synaptic stimulation, increases ATP availability from mitochondria through regulation of mitochondrial membrane ATP synthase F(1)F(0) activity and regulates endocytic vesicle retrieval in hippocampal neurons through association with DMN1L and stimulation of its GTPase activity in synaptic vesicles. May attenuate inflammation impairing NLRP1-inflammasome activation, hence CASP1 activation and IL1B release (PubMed:17418785).Isoform Bcl-X(S) promotes apoptosis.
Gene Name:
BCL2L1
Uniprot ID:
Q07817
Molecular Weight:
26048.8 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Dissociation2700 uMNot AvailableBindingDB 50308551
References
  1. Barelier S, Pons J, Marcillat O, Lancelin JM, Krimm I: Fragment-based deconstruction of Bcl-xL inhibitors. J Med Chem. 2010 Mar 25;53(6):2577-88. doi: 10.1021/jm100009z. [20192224 ]
General Function:
Scaffold protein binding
Specific Function:
Receptor for extracellular adenine nucleotides such as ATP and ADP. In platelets binding to ADP leads to mobilization of intracellular calcium ions via activation of phospholipase C, a change in platelet shape, and probably to platelet aggregation.
Gene Name:
P2RY1
Uniprot ID:
P47900
Molecular Weight:
42071.08 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.28 uMNVS_GPCR_hPY2Novascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Zinc ion binding
Specific Function:
Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the ACOX1 and P450 genes. Transactivation activity requires heterodimerization with RXRA and is antagonized by NR2C2. May be required for the propagation of clock information to metabolic pathways regulated by PER2.
Gene Name:
PPARA
Uniprot ID:
Q07869
Molecular Weight:
52224.595 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC503.24 uMNVS_NR_hPPARaNovascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Prostaglandin e receptor activity
Specific Function:
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(s) proteins that stimulate adenylate cyclase. The subsequent raise in intracellular cAMP is responsible for the relaxing effect of this receptor on smooth muscle.
Gene Name:
PTGER2
Uniprot ID:
P43116
Molecular Weight:
39759.945 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC504.44 uMBSK_LPS_PGE2_downBioSeek
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular Weight:
56277.81 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC508.65 uMCLZD_CYP2B6_48CellzDirect
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]