2,3-ジヒドロキシ安息香酸

2,3-ジヒドロキシ安息香酸
	IUPAC名 2,3-Dihydroxybenzoic acid
	別称 Hypogallic acid; 2-Pyrocatechuic acid; o-Pyrocatechuic acid
識別情報
略称	2,3-DHBA; 2,3-DHB
CAS登録番号	303-38-8
PubChem	19
ChemSpider	18
DrugBank	DB01672
KEGG	C00196
ChEBI	CHEBI:18026 ;
ChEMBL	CHEMBL1432
	SMILES O=C(O)c1cccc(O)c1O; c1cc(c(c(c1)O)O)C(=O)O;
	InChI InChI=1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11) Key: GLDQAMYCGOIJDV-UHFFFAOYSA-N ; InChI=1/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11) Key: GLDQAMYCGOIJDV-UHFFFAOYAE;
特性
化学式	C7H6O4
モル質量	154.12 g mol−1
精密質量	154.026609 u
外観	無色固体
融点	204-206 °C, 477-479 K, 399-403 °F
水への溶解度	低
関連する物質
関連物質	ジヒドロキシ安息香酸
	特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

2,3-ジヒドロキシ安息香酸(2,3-Dihydroxybenzoic acid)は、アメダマノキ(Phyllanthus acidus)^[1]やオオサンショウモ(Salvinia molesta)^[2]で見られる天然のフェノールである。オオミイヌカンコ(Flacourtia inermis)の果実にも豊富に含まれる。ジヒドロキシ安息香酸の異性体の1つ、無色の固体である。シキミ酸経路で合成され、鉄イオンと強い錯体を形成して細菌内に吸収させる分子であるシデロフォアに取り込まれる。2,3-ジヒドロキシ安息香酸は、脱プロトン化して鉄に強く結合するカテコール基と、環がアミド結合を通じて様々な構造に結合するカルボン酸から構成される。親和性が高く有名なシデロフォアには、エンテロバクチンがある。これは、3つの2,3-ジヒドロキシ安息香酸置換基がセリンのデプシペプチドに結合した構造を持つ^[3]^[4] 。

鉄キレート剤^[5]や抗菌剤^[6]^[7]^[8]として利用できる可能性がある。

また、2,3-ジヒドロキシ安息香酸は、ヒトのアスピリン代謝物の1つである^[9]。

出典

^ Sousa M, Ousingsawat J, Seitz R, et al. (January 2007). “An extract from the medicinal plant Phyllanthus acidus and its isolated compounds induce airway chloride secretion: A potential treatment for cystic fibrosis”. Mol. Pharmacol. 71 (1): 366–76. doi:10.1124/mol.106.025262. PMID 17065237.
^ “Phenolic and other constituents of fresh water fern Salvinia molesta”. Phytochemistry 69 (4): 1018–23. (February 2008). doi:10.1016/j.phytochem.2007.10.028. PMID 18177906.
^ I. G. O'Brien, G. B. Cox, F. Gibson (1970). “Biologically active compounds containing 2,3-dihydroxybenzoic acid and serine formed by Escherichia coli”. Biochimica et Biophysica Acta 201 (3): 453–60. doi:10.1016/0304-4165(70)90165-0. PMID 4908639.
^ Young, I.G.; Gibson, F. (1969). “Regulation of the enzymes involved in the biosynthesis of 2,3-dihydroxybenzoic acid in Aerobacter aerogenes and Escherichia coli”. Biochimica et Biophysica Acta (BBA) - General Subjects 177 (3): 401–411. doi:10.1016/0304-4165(69)90302-X. ISSN 03044165.
^ J. H. Graziano, R. W. Grady and A. Cerami (1974). “The identification of 2,3-dihroxybenzoic acid as a potentially useful iron-chelating drug”. JPET 190 (3): 570–575.
^ Shibumon George, Benny PJ, Sunny Kuriakose, Cincy George (2011). “Antibiotic activity of 2, 3-dihydroxybenzoic acid isolated from Flacourtia inermis fruit against multidrug resistant bacteria”. Asian Journal of Pharmaceutical and Clinical Research 4 (1).
^ Benny PJ, George Shibumon, Kuriakose Sunny, George Cincy (2010). “2, 3-Dihydroxybenzoic Acid: An Effective Antifungal Agent Isolated from Flacourtia inermis Fruit”. International Journal of Pharmaceutical and Clinical Research 2 (3): 101-105.
^ George Shibumon, Benny PJ, Kuriakose Sunny, George Cincy, Gopalakrishnan Sarala (2011). “Antiprotozoal activity of 2, 3-dihydroxybenzoic acid isolated from the fruit extracts of Flacourtia inermis Roxb”. Medicinal Plants - International Journal of Phytomedicines and Related Industries 3 (3): 237-241. doi:10.5958/j.0975-4261.3.3.038.
^ Grootveld, Martin; Halliwell, Barry (1988). “2,3-Dihydroxybenzoic acid is a product of human aspirin metabolism”. Biochemical Pharmacology 37 (2): 271–280. doi:10.1016/0006-2952(88)90729-0. ISSN 00062952.

[1] Sousa M, Ousingsawat J, Seitz R, et al. (January 2007). “An extract from the medicinal plant Phyllanthus acidus and its isolated compounds induce airway chloride secretion: A potential treatment for cystic fibrosis”. Mol. Pharmacol. 71 (1): 366–76. doi:10.1124/mol.106.025262. PMID 17065237.

[2] “Phenolic and other constituents of fresh water fern Salvinia molesta”. Phytochemistry 69 (4): 1018–23. (February 2008). doi:10.1016/j.phytochem.2007.10.028. PMID 18177906.

[3] I. G. O'Brien, G. B. Cox, F. Gibson (1970). “Biologically active compounds containing 2,3-dihydroxybenzoic acid and serine formed by Escherichia coli”. Biochimica et Biophysica Acta 201 (3): 453–60. doi:10.1016/0304-4165(70)90165-0. PMID 4908639.

[4] Young, I.G.; Gibson, F. (1969). “Regulation of the enzymes involved in the biosynthesis of 2,3-dihydroxybenzoic acid in Aerobacter aerogenes and Escherichia coli”. Biochimica et Biophysica Acta (BBA) - General Subjects 177 (3): 401–411. doi:10.1016/0304-4165(69)90302-X. ISSN 03044165.

[5] J. H. Graziano, R. W. Grady and A. Cerami (1974). “The identification of 2,3-dihroxybenzoic acid as a potentially useful iron-chelating drug”. JPET 190 (3): 570–575.

[6] Shibumon George, Benny PJ, Sunny Kuriakose, Cincy George (2011). “Antibiotic activity of 2, 3-dihydroxybenzoic acid isolated from Flacourtia inermis fruit against multidrug resistant bacteria”. Asian Journal of Pharmaceutical and Clinical Research 4 (1).

[7] Benny PJ, George Shibumon, Kuriakose Sunny, George Cincy (2010). “2, 3-Dihydroxybenzoic Acid: An Effective Antifungal Agent Isolated from Flacourtia inermis Fruit”. International Journal of Pharmaceutical and Clinical Research 2 (3): 101-105.

[8] George Shibumon, Benny PJ, Kuriakose Sunny, George Cincy, Gopalakrishnan Sarala (2011). “Antiprotozoal activity of 2, 3-dihydroxybenzoic acid isolated from the fruit extracts of Flacourtia inermis Roxb”. Medicinal Plants - International Journal of Phytomedicines and Related Industries 3 (3): 237-241. doi:10.5958/j.0975-4261.3.3.038.

[9] Grootveld, Martin; Halliwell, Barry (1988). “2,3-Dihydroxybenzoic acid is a product of human aspirin metabolism”. Biochemical Pharmacology 37 (2): 271–280. doi:10.1016/0006-2952(88)90729-0. ISSN 00062952.

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