Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2020-04-28 16:47:45 UTC |
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Update Date | 2022-03-07 03:18:20 UTC |
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HMDB ID | HMDB0240642 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | 3,5-Di-tert-butyl-4-hydroxybenzoic acid |
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Description | 3,5-Di-tert-butyl-4-hydroxybenzoic acid, also known as BHT-COOH or 4-carboxy-2,6-di-tert-butylphenol, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. BHT-COOH is a metabolite of 2,6-di-tert-butyl-4-methylphenol (BHA), a synthetic phenolic antioxidant (SPA). SPAs are a family of chemicals used widely in foods, polymers, and cosmetics as radical trapping agents to slow down degradation due to oxidation. Given their widespread use, human exposure is unavoidable and there is public concern regarding environmental contamination by these chemicals. BHT-OH was detected in human urine (PMID: 31265952 ). |
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Structure | CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)C(O)=O InChI=1S/C15H22O3/c1-14(2,3)10-7-9(13(17)18)8-11(12(10)16)15(4,5)6/h7-8,16H,1-6H3,(H,17,18) |
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Synonyms | Value | Source |
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3,5-Di-tert-butyl-4-hydroxybenzoate | Generator | BHT-COOH | HMDB | 2,6-Di-tert-butyl-4-carboxyphenol | HMDB | 3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzoic acid | HMDB | 4-Carboxy-2,6-di-tert-butylphenol | HMDB | 4-Hydroxy-3,5-di-tert-butylbenzoic acid | HMDB | 3,5-Di-tert-butyl-4-hydroxybenzoic acid | MeSH |
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Chemical Formula | C15H22O3 |
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Average Molecular Weight | 250.338 |
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Monoisotopic Molecular Weight | 250.156894568 |
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IUPAC Name | 3,5-di-tert-butyl-4-hydroxybenzoic acid |
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Traditional Name | 3,5-di-tert-butyl-4-hydroxybenzoic acid |
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CAS Registry Number | 1421-49-4 |
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SMILES | CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)C(O)=O |
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InChI Identifier | InChI=1S/C15H22O3/c1-14(2,3)10-7-9(13(17)18)8-11(12(10)16)15(4,5)6/h7-8,16H,1-6H3,(H,17,18) |
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InChI Key | YEXOWHQZWLCHHD-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl 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 | Benzoic acids and derivatives |
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Direct Parent | Hydroxybenzoic acid derivatives |
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Alternative Parents | |
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Substituents | - Hydroxybenzoic acid
- Phenylpropane
- Benzoic acid
- Benzoyl
- Phenol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | Not Available |
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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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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3,5-Di-tert-butyl-4-hydroxybenzoic acid,1TMS,isomer #1 | CC(C)(C)C1=CC(C(=O)O)=CC(C(C)(C)C)=C1O[Si](C)(C)C | 2015.1 | Semi standard non polar | 33892256 | 3,5-Di-tert-butyl-4-hydroxybenzoic acid,1TMS,isomer #2 | CC(C)(C)C1=CC(C(=O)O[Si](C)(C)C)=CC(C(C)(C)C)=C1O | 1906.7 | Semi standard non polar | 33892256 | 3,5-Di-tert-butyl-4-hydroxybenzoic acid,2TMS,isomer #1 | CC(C)(C)C1=CC(C(=O)O[Si](C)(C)C)=CC(C(C)(C)C)=C1O[Si](C)(C)C | 2078.1 | Semi standard non polar | 33892256 | 3,5-Di-tert-butyl-4-hydroxybenzoic acid,1TBDMS,isomer #1 | CC(C)(C)C1=CC(C(=O)O)=CC(C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C | 2243.9 | Semi standard non polar | 33892256 | 3,5-Di-tert-butyl-4-hydroxybenzoic acid,1TBDMS,isomer #2 | CC(C)(C)C1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(C(C)(C)C)=C1O | 2143.5 | Semi standard non polar | 33892256 | 3,5-Di-tert-butyl-4-hydroxybenzoic acid,2TBDMS,isomer #1 | CC(C)(C)C1=CC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C | 2507.8 | Semi standard non polar | 33892256 |
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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 - 3,5-Di-tert-butyl-4-hydroxybenzoic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | 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 - 3,5-Di-tert-butyl-4-hydroxybenzoic acid 10V, Positive-QTOF | splash10-0udi-0090000000-7467e42064ee08ac42cb | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,5-Di-tert-butyl-4-hydroxybenzoic acid 20V, Positive-QTOF | splash10-0f89-0390000000-974088ad571180615e1f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,5-Di-tert-butyl-4-hydroxybenzoic acid 40V, Positive-QTOF | splash10-0a7i-3690000000-682e13e87cc4e4ec8606 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,5-Di-tert-butyl-4-hydroxybenzoic acid 10V, Negative-QTOF | splash10-0002-0090000000-77e0271550d3898a3fe4 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,5-Di-tert-butyl-4-hydroxybenzoic acid 20V, Negative-QTOF | splash10-0a4j-0190000000-34a21f0d7a041ace1a6d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,5-Di-tert-butyl-4-hydroxybenzoic acid 40V, Negative-QTOF | splash10-0a4j-1890000000-2dce0525ad25dd5303a7 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,5-Di-tert-butyl-4-hydroxybenzoic acid 10V, Negative-QTOF | splash10-0a4i-0090000000-6a76724ca68c443d673e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,5-Di-tert-butyl-4-hydroxybenzoic acid 20V, Negative-QTOF | splash10-0a4j-0090000000-250bf2625d573b97ae7a | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,5-Di-tert-butyl-4-hydroxybenzoic acid 40V, Negative-QTOF | splash10-000i-0960000000-02b30cc39bf8c672b6a0 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,5-Di-tert-butyl-4-hydroxybenzoic acid 10V, Positive-QTOF | splash10-0udi-0290000000-114a124b6a8e49fc6628 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,5-Di-tert-butyl-4-hydroxybenzoic acid 20V, Positive-QTOF | splash10-0udj-0590000000-35eb44b51adc0107f920 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,5-Di-tert-butyl-4-hydroxybenzoic acid 40V, Positive-QTOF | splash10-0a59-8900000000-1ef30a3afc57be07b7df | 2021-09-24 | Wishart Lab | View Spectrum |
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