2-Biphenylol
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Basic Info
| Common Name | 2-Biphenylol(F05180) |
| 2D Structure | |
| Description | 2-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 <ht>HMJ12-A</ht>. 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. |
| FRCD ID | F05180 |
| CAS Number | 90-43-7 |
| PubChem CID | 7017 |
| Formula | C12H10O |
| IUPAC Name | 2-phenylphenol |
| InChI Key | LLEMOWNGBBNAJR-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H10O/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9,13H |
| Canonical SMILES | C1=CC=C(C=C1)C2=CC=CC=C2O |
| Isomeric SMILES | C1=CC=C(C=C1)C2=CC=CC=C2O |
| Synonyms |
2-Hydroxybiphenyl
o-Hydroxydiphenyl
2-Phenylphenol
90-43-7
O-PHENYLPHENOL
Biphenyl-2-ol
2-Biphenylol
o-Hydroxybiphenyl
2-Hydroxydiphenyl
Phenylphenol
|
| Classifies |
Pesticide
Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Biphenyls and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Biphenyls and derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Biphenyl - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound |
| Description | This compound 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. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 170.211 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 1 |
| Complexity | 149 |
| Monoisotopic Mass | 170.073 |
| Exact Mass | 170.073 |
| XLogP | 3.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 13 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9459 |
| Human Intestinal Absorption | HIA+ | 1.0000 |
| Caco-2 Permeability | Caco2+ | 0.9127 |
| P-glycoprotein Substrate | Non-substrate | 0.7749 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8914 |
| Non-inhibitor | 0.9499 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8475 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8971 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7297 |
| CYP450 2D6 Substrate | Non-substrate | 0.8420 |
| CYP450 3A4 Substrate | Non-substrate | 0.6973 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.8690 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.6231 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9473 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8429 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9628 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7255 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9087 |
| Non-inhibitor | 0.8603 | |
| AMES Toxicity | Non AMES toxic | 0.9325 |
| Carcinogens | Non-carcinogens | 0.7817 |
| Fish Toxicity | High FHMT | 0.9677 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9884 |
| Honey Bee Toxicity | High HBT | 0.7398 |
| Biodegradation | Not ready biodegradable | 0.7893 |
| Acute Oral Toxicity | III | 0.8400 |
| Carcinogenicity (Three-class) | Non-required | 0.5193 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.9306 | LogS |
| Caco-2 Permeability | 1.7139 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.9614 | LD50, mol/kg |
| Fish Toxicity | 0.6640 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.2152 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Citrus fruits | 0110000 | European Union | 5 | 30/07/2014 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 5 | 30/07/2014 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 5 | 30/07/2014 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 5 | 30/07/2014 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 5 | 30/07/2014 | |
| Others (2) | 0110990 | European Union | 5 | 30/07/2014 | |
| Tree nuts | 0120000 | European Union | 0.1* | 30/07/2014 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.1* | 30/07/2014 | |
| Brazil nuts | 0120020 | European Union | 0.1* | 30/07/2014 | |
| Cashew nuts | 0120030 | European Union | 0.1* | 30/07/2014 | |
| Chestnuts | 0120040 | European Union | 0.1* | 30/07/2014 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.1* | 30/07/2014 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.1* | 30/07/2014 | |
| Macadamias | 0120070 | European Union | 0.1* | 30/07/2014 | |
| Pecans (Hickory nuts,) | 0120080 | European Union | 0.1* | 30/07/2014 | |
| Kidney | 1014040 | European Union | 0.05* | 30/07/2014 | |
| Pine nut kernels (Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels ... | 0120090 | European Union | 0.1* | 30/07/2014 | |
| Pistachios | 0120100 | European Union | 0.1* | 30/07/2014 | |
| Walnuts | 0120110 | European Union | 0.1* | 30/07/2014 | |
| Others (2) | 0120990 | European Union | 0.1* | 30/07/2014 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| The potential of organic substrates based on mushroom substrate and straw todissipate fungicides contained in effluents from the fruit-packaging industry -Is there a role for Pleurotus ostreatus? | Ecotoxicol Environ Saf | 2016 Feb | 26624931 |
| Simultaneous Determination of Seven Kinds of Fungicides in Citrus Fruits by GasChromatograghy/Mass Spectrometry. | Shokuhin Eiseigaku Zasshi | 2016 | 27558228 |
| Dissipation, metabolism and sorption of pesticides used in fruit-packagingplants: Towards an optimized depuration of their pesticide-contaminatedagro-industrial effluents. | Sci Total Environ | 2015 Oct 15 | 26042894 |
| [Rapid Determination of Seven Fungicides in Citrus Fruits]. | Shokuhin Eiseigaku Zasshi | 2015 | 26537653 |
| Separation of a binary mixture of pesticides in fruits using a flow-throughoptosensor. | Talanta | 2013 Oct 15 | 24054619 |
| [Study of residue preservatives thiabendazole, o-phenylphenol and diphenyl infruits and vegetables by SPE-separation technology]. | Guang Pu Xue Yu Guang Pu Fen Xi | 2012 Aug | 23156781 |
| Automated on-line column-switching HPLC-MS/MS method with peak focusing formeasuring parabens, triclosan, and other environmental phenols in human milk. | Anal Chim Acta | 2008 Aug 1 | 18602546 |
| Efflux pump activity in fluoroquinolone and tetracycline resistant Salmonella andE. coli implicated in reduced susceptibility to household antimicrobial cleaning agents. | Int J Food Microbiol | 2007 Feb 15 | 17126442 |
| [Inhibitory effect of zinc on beta-hexosaminidase release from RBL-2H3 cells bysynthetic chemicals]. | Shokuhin Eiseigaku Zasshi | 2004 Apr | 15272608 |
| Solid-phase microextraction liquid chromatography/tandem mass spectrometry todetermine postharvest fungicides in fruits. | Anal Chem | 2003 Jul 15 | 14570216 |
| Off-line solid-phase microextraction and capillary electrophoresis massspectrometry to determine acidic pesticides in fruits. | Anal Chem | 2003 Feb 1 | 12585470 |
| Monitoring of five postharvest fungicides in fruit and vegetables by matrixsolid-phase dispersion and liquid chromatography/mass spectrometry. | J AOAC Int | 2002 May-Jun | 12083263 |
| Detection and characterization of DNA adducts formed from metabolites of thefungicide ortho-phenylphenol. | J Agric Food Chem | 2002 May 22 | 12010010 |
| Determination of fungicide residues in fruits and vegetables by liquidchromatography-atmospheric pressure chemical ionization mass spectrometry. | J Chromatogr A | 2002 Feb 22 | 11883656 |
| Estimation of concentrations of antifungal agents allowed as food additives infoods and their daily intake based on official inspection results in Japan infiscal year 1998. | Shokuhin Eiseigaku Zasshi | 2002 Feb | 11998320 |
| Comparative in vitro-in vivo percutaneous penetration of the fungicideortho-phenylphenol. | Regul Toxicol Pharmacol | 2002 Apr | 12052004 |
| An analysis of the possibility for health implications of joint actions and interactions between food additives. | Regul Toxicol Pharmacol | 2000 Feb | 10715227 |
| Toxicological profile for o-phenylphenol and its sodium salt. | J Appl Toxicol | 1998 Jul-Aug | 9719426 |
| Determination of o-phenylphenol, diphenylamine, and propargite pesticide residuesin selected fruits and vegetables by gas chromatography/mass spectrometry. | J AOAC Int | 1997 May-Jun | 9170661 |
| Cytotoxicity of food preservatives in cultured rat hepatocytes loaded withlinolenic acid. | Toxicology | 1997 Jun 6 | 9160106 |
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
References
- 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
References
- 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
References
- 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
References
- 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
References
- 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 ]