2,4-Dihydroxybenzoic acid
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Preferred IUPAC name 2,4-Dihydroxybenzoic acid | |
Other names β-Resorcylic acid β-Resorcinolic acid p-Hydroxysalicylic acid 2,4-DHBA | |
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ECHA InfoCard | 100.001.770 |
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InChI
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Properties | |
Chemical formula | C7H6O4 |
Molar mass | 154.12 g/mol |
Melting point | 229 °C (444 °F; 502 K)[2] |
Acidity (pKa) | 3.11, 8.55, 14.0[1] |
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Hazard statements | H315, H319, H335 |
Precautionary statements | P261, P280, P302+P352, P305+P351+P338 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references |
Chemical compound
2,4-Dihydroxybenzoic acid (β-resorcylic acid) is a dihydroxybenzoic acid.
As a resorcylic acid, it is one of the three isomeric crystalline acids that are both carboxyl derivatives of resorcinol and dihydroxy derivatives of benzoic acid.[4] Synthesis from resorcinol is via the Kolbe-Schmitt reaction.[5]
It is a degradation product of cyanidin glycosides from tart cherries in cell cultures.[6] It is also a metabolite found in human plasma after cranberry juice consumption.[7]
References
- ^ Haynes, p. 5.91
- ^ Haynes, p. 3.190
- ^ GHS: GESTIS 492493
- ^ Resorcyclic acid on merriam-webster on-line dictionary
- ^ Becker, Heinz G. O., ed. (1993). Organikum: organisch-chemisches Grundpraktikum (in German) (19th (rev. and expanded) ed.). Leipzig: Johann Ambrosius Barth [de]. pp. 351–352. ISBN 978-3-335-00343-4.
- ^ Seeram, Navindra P.; Bourquin, Leslie D.; Nair, Muraleedharan G. (2001). "Degradation Products of Cyanidin Glycosides from Tart Cherries and Their Bioactivities". Journal of Agricultural and Food Chemistry. 49 (10): 4924–4929. doi:10.1021/jf0107508. PMID 11600045.
- ^ Zhang, Kai; Zuo, Yuegang (2004). "GC-MS Determination of Flavonoids and Phenolic and Benzoic Acids in Human Plasma after Consumption of Cranberry Juice". Journal of Agricultural and Food Chemistry. 52 (2): 222–227. doi:10.1021/jf035073r. PMID 14733499.
Cited sources
- Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. ISBN 9781498754293.
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Phenolic acids (C6-C1) and their glycosides
- 3-Hydroxybenzoic acid
- 4-Hydroxybenzoic acid
- Salicylic acid (2-Hydroxybenzoic acid)
Glycosides |
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Alkylated |
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- 2,3-Dihydroxybenzoic acid (Hypogallic acid)
- 2,4-Dihydroxybenzoic acid
- 2,5-Dihydroxybenzoic acid (Gentisic acid)
- 2,6-Dihydroxybenzoic acid
- 3,4-Dihydroxybenzoic acid (Protocatechuic acid)
- 3,5-Dihydroxybenzoic acid
Alkylated |
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Glycosides | |
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Alkylated |
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