Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2021-09-11 03:27:19 UTC |
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Update Date | 2021-09-26 22:59:35 UTC |
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HMDB ID | HMDB0248991 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | Benzilic acid |
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Description | benzilic acid, also known as benzilsaeure or a-phenylmandelate, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. It is a white crystalline aromatic acid, soluble in many primary alcohols. Benzilic acid is used in the manufacture of glycollate pharmaceuticals including Clidinium, Dilantin, and Flutropium, which are antagonists of the muscarinic acetylcholine receptors. Another preparation, performed by Liebig in 1838, is the dimerization of benzaldehyde, to benzil, which is transformed to the product by the benzilic acid rearrangement reaction. Benzilic acid can be prepared by heating mixture of benzil, ethanol and potassium hydroxide. benzilic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Benzilic acid is an organic compound with formula C14H12O3 or (C6H5)2(HO)C(COOH). It is used in manufacture of the incapacitating agent 3-quinuclidinyl benzilate (BZ) and is regulated by the Chemical Weapons Convention. It is also monitored by law enforcement agencies of many countries, because of its use in the manufacture in hallucinogenic drugs. This compound has been identified in human blood as reported by (PMID: 31557052 ). Benzilic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Benzilic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources. |
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Structure | OC(=O)C(O)(C1=CC=CC=C1)C1=CC=CC=C1 InChI=1S/C14H12O3/c15-13(16)14(17,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,17H,(H,15,16) |
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Synonyms | Value | Source |
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2-Hydroxy-2,2-diphenylacetic acid | ChEBI | Acide diphenylhydroxyacetique | ChEBI | alpha,alpha-Diphenyl-alpha-hydroxyacetic acid | ChEBI | alpha,alpha-Diphenylglycolic acid | ChEBI | alpha-Hydroxy-2,2-diphenylacetic acid | ChEBI | alpha-Hydroxy-alpha-phenylbenzeneacetic acid | ChEBI | alpha-Phenylmandelic acid | ChEBI | Benzilsaeure | ChEBI | Diphenylglycolic acid | ChEBI | 2-Hydroxy-2,2-diphenylacetate | Generator | a,a-Diphenyl-a-hydroxyacetate | Generator | a,a-Diphenyl-a-hydroxyacetic acid | Generator | alpha,alpha-Diphenyl-alpha-hydroxyacetate | Generator | Α,α-diphenyl-α-hydroxyacetate | Generator | Α,α-diphenyl-α-hydroxyacetic acid | Generator | a,a-Diphenylglycolate | Generator | a,a-Diphenylglycolic acid | Generator | alpha,alpha-Diphenylglycolate | Generator | Α,α-diphenylglycolate | Generator | Α,α-diphenylglycolic acid | Generator | a-Hydroxy-2,2-diphenylacetate | Generator | a-Hydroxy-2,2-diphenylacetic acid | Generator | alpha-Hydroxy-2,2-diphenylacetate | Generator | Α-hydroxy-2,2-diphenylacetate | Generator | Α-hydroxy-2,2-diphenylacetic acid | Generator | a-Hydroxy-a-phenylbenzeneacetate | Generator | a-Hydroxy-a-phenylbenzeneacetic acid | Generator | alpha-Hydroxy-alpha-phenylbenzeneacetate | Generator | Α-hydroxy-α-phenylbenzeneacetate | Generator | Α-hydroxy-α-phenylbenzeneacetic acid | Generator | a-Phenylmandelate | Generator | a-Phenylmandelic acid | Generator | alpha-Phenylmandelate | Generator | Α-phenylmandelate | Generator | Α-phenylmandelic acid | Generator | Diphenylglycolate | Generator | Benzilate | Generator | DPHEAc | MeSH | 2,2-Diphenyl-2-hydroxyethanoic acid | MeSH |
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Chemical Formula | C14H12O3 |
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Average Molecular Weight | 228.2433 |
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Monoisotopic Molecular Weight | 228.07864425 |
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IUPAC Name | 2-hydroxy-2,2-diphenylacetic acid |
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Traditional Name | benzilic acid |
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CAS Registry Number | Not Available |
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SMILES | OC(=O)C(O)(C1=CC=CC=C1)C1=CC=CC=C1 |
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InChI Identifier | InChI=1S/C14H12O3/c15-13(16)14(17,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,17H,(H,15,16) |
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InChI Key | UKXSKSHDVLQNKG-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Diphenylmethanes |
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Direct Parent | Diphenylmethanes |
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Alternative Parents | |
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Substituents | - Diphenylmethane
- Hydroxy acid
- Alpha-hydroxy acid
- Tertiary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Aromatic alcohol
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Benzilic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-001i-0900000000-3f167fbecb453382e628 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Benzilic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Benzilic acid GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Benzilic acid GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Benzilic acid GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Benzilic acid GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Benzilic acid GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Benzilic acid GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-11-03 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzilic acid 10V, Positive-QTOF | splash10-03di-0190000000-efaac40d8a455261b420 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzilic acid 20V, Positive-QTOF | splash10-01t9-5490000000-034f3edee73420aeddaa | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzilic acid 40V, Positive-QTOF | splash10-004i-9100000000-2b02c41a39372f9d4258 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzilic acid 10V, Negative-QTOF | splash10-001i-0900000000-2565412c6fe1c60ab16f | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzilic acid 20V, Negative-QTOF | splash10-001i-1900000000-5fe93bf8c00d775713c1 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Benzilic acid 40V, Negative-QTOF | splash10-0a4i-1900000000-622ef9be868df501ca20 | 2021-10-12 | Wishart Lab | View Spectrum |
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