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Daidzin

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Not to be confused withDaidzein.

Daidzin
Names

IUPAC name 7-(β-D-Glucopyranosyloxy)-4′-hydroxyisoflavone
Systematic IUPAC name 7-{[(2S,3R,4S,5S,6R)-6-(Hydroxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Other names Daidzoside Daidzein 7-glucoside Daidzein-7-glucoside Daidzein 7-O-glucoside daidzein 7-O-beta-D-glucoside
Identifiers
CAS Number	552-66-9^Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:42202^N
ChEMBL	ChEMBL486422^N
ChemSpider	97088^N
ECHA InfoCard	100.107.506
KEGG	C10216^Y
PubChem CID	107971
UNII	4R2X91A5M5^Y
CompTox Dashboard(EPA)	DTXSID00862180
InChI InChI=1S/C21H20O9/c22-8-16-18(25)19(26)20(27)21(30-16)29-12-5-6-13-15(7-12)28-9-14(17(13)24)10-1-3-11(23)4-2-10/h1-7,9,16,18-23,25-27H,8H2/t16-,18-,19+,20-,21-/m1/s1^N Key: KYQZWONCHDNPDP-QNDFHXLGSA-N^N InChI=1/C21H20O9/c22-8-16-18(25)19(26)20(27)21(30-16)29-12-5-6-13-15(7-12)28-9-14(17(13)24)10-1-3-11(23)4-2-10/h1-7,9,16,18-23,25-27H,8H2/t16-,18-,19+,20-,21-/m1/s1 Key: KYQZWONCHDNPDP-QNDFHXLGBS
SMILES c1cc(ccc1c2coc3cc(ccc3c2=O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O O=C3c4ccc(OC1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)cc4O/C=C3/c2ccc(O)cc2
Properties
Chemical formula	C₂₁H₂₀O₉
Molar mass	416.38
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

Daidzin is a naturalorganic compound in the class ofphytochemicals known asisoflavones. Daidzin can be found in Chinese plantkudzu (Pueraria lobata, Fabaceae) and fromsoybean leaves.^[1]

Daidzin is the 7-O-glucoside ofdaidzein.

Daidzin has shown the potential for the treatment of alcohol dependency (antidipsotropic) based on animal models.^[2]^[3]

List of plants that contain the chemical

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Notes and references

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^Osman, S; Fett, W (1983). "Isoflavone glucoside stress metabolites of soybean leaves".Phytochemistry.22 (9): 1921.Bibcode:1983PChem..22.1921O.doi:10.1016/0031-9422(83)80013-2.
^Rezvani, A; Overstreet, David H; Perfumi, Marina; Massi, Maurizio (2003). "Plant derivatives in the treatment of alcohol dependency".Pharmacology Biochemistry and Behavior.75 (3):593–606.doi:10.1016/S0091-3057(03)00124-2.PMID 12895677.S2CID 23298356.
^Keung WM; Vallee BL (February 1998). "Kudzu root: an ancient Chinese source of modern antidipsotropic agents".Phytochemistry.47 (4):499–506.Bibcode:1998PChem..47..499K.doi:10.1016/S0031-9422(97)00723-1.PMID 9461670.
^Pongkitwitoon B; Sakamoto S; Tanaka H; et al. (December 2009). "Enzyme-Linked Immunosorbent Assay for Total Isoflavonoids in Pueraria candollei Using Anti-Puerarin and Anti-Daidzin Polyclonal Antibodies".Planta Medica.76 (8):831–6.doi:10.1055/s-0029-1240725.PMID 20033865.
^Jin WS; Tan YY; Chen YG; Wang Y (January 2003). "[Determination of puerarin, daidzin and daidzein in root of Pueraria lobata of different origin by HPLC]".Zhongguo Zhong Yao Za Zhi (in Chinese).28 (1):49–51.PMID 15015267.
^Zhou HY; Wang JH; Yan FY (May 2007). "[Separation and determination of puerarin, daidzin and daidzein in stems and leaves of Pueraria thomsonii by RP-HPLC]".Zhongguo Zhong Yao Za Zhi (in Chinese).32 (10):937–9.PMID 17655152.
^Park EK; Shin J; Bae EA; Lee YC; Kim DH (December 2006)."Intestinal bacteria activate estrogenic effect of main constituents puerarin and daidzin of Pueraria thunbergiana".Biological & Pharmaceutical Bulletin.29 (12):2432–5.doi:10.1248/bpb.29.2432.PMID 17142977.

v t e Isoflavones and theirglycosides
Isoflavones	Daidzein Genistein Orobol
O-methylated isoflavones	Biochanin A Calycosin Formononetin Glycitein Irigenin 5-O-methylgenistein Pratensein Prunetin Psi-tectorigenin Retusin Tectorigenin
Glycosides	Daidzin Genistin Iridin Mirificin Ononin Puerarin Sophoricoside Tectoridin
Prenylated isoflavones	Bidwillol A Derrubone Luteone 7-O-Methylluteone Wighteone
Pyranoisoflavones	Alpinumisoflavone Barbigerone Di-O-methylalpinumisoflavone 4'-methyl-alpinumisoflavone
Derivatives	Anagyroidisoflavone A andB Irilone Pseudobaptigenin Rotenoids
Synthetic	Ipriflavone
Category

v t e Monoaminergic neurotoxins
Dopaminergic	2′-CH₃-MPTP (2′-methyl-MPTP) 2,4,5-THA 2,4,5-THMA 4-MMA 5-S-Cysteinyldopamine 5,6-DHT 6-Hydroxydopa 6-OHDA quinone 6,7-DHT ALDH inhibitors (e.g.,disulfiram,methylmercury) Amphetamine Benomyl Daidzin Dieldrin DOPA quinone DOPAL DOPAL quinone Dopamine Dopamine quinone Fenpropathrin Haloperidol HPP⁺ HPTP Imidazole propionate (ImP) Mancozeb Maneb Mephedrone Methamphetamine Methcathinone Methylone MPP⁺ (cyperquat) MPTP N-Methylnorsalsolinol Norsalsolinol Oxidopamine (6-OHDA) Paraquat Rotenone Salsolinol Ziram
Noradrenergic	2′-NH₂-MPTP (2′-amino-MPTP) 2,4,5-THA 4,5-DHT 5,6-DHT 5,7-DHT 6-Hydroxydopa DOPEGAL DSP-4 MDA (tenamfetamine) Oxidopamine (6-OHDA) Xylamine
Serotonergic	2′-NH₂-MPTP (2′-amino-MPTP) 2,4-DCA 2,4,5-THA 2,4,5-THMA 3-CA 3,4-DCA 4-CAB (α-ethyl-PCA) 4-CMA 4-HO-5-MeO-T 4,5-DHT 5-IAI 5-MAPB 5-MeO-DiPT 5,6-DHT 5,7-DHT 6,7-DHT αET ETAI Fenfluramine Haloperidol HHA (α-methyldopamine) HHMA (α-methylepinine, α,N-dimethyldopamine) HPP⁺ HPTP MBDB MDA (tenamfetamine) MDMA (midomafetamine) Mephedrone Methamphetamine Methylone Norfenfluramine PBA PBMA PCA PCMA PIA TAI
Unsorted	2,5-DDM-DOM 5-HIAL RHPP⁺ RHPTP
See also:Receptor/signaling modulators •Adrenergics •Dopaminergics •Melatonergics •Serotonergics •Monoamine reuptake inhibitors •Monoamine releasing agents •Monoamine metabolism modulators

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List of plants that contain the chemical

Notes and references

See also