1.0 2010-04-08 22:05:24 UTC 2025-11-18 22:37:54 UTC FDB002501 Vitexin Vitexin is a member of the class of compounds known as flavonoid 8-c-glycosides. Flavonoid 8-c-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Vitexin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Vitexin can be found in a number of food items such as flaxseed, prairie turnip, mung bean, and tree fern, which makes vitexin a potential biomarker for the consumption of these food products. Vitexin is an apigenin flavone glucoside, a chemical compound found in the passion flower, Vitex agnus-castus (chaste tree or chasteberry), in the Phyllostachys nigra bamboo leaves, in the pearl millet (Pennisetum millet), and in Hawthorn . 8-b-D-Glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9CI 8-Glucopyranosyl-4',5,7-trihydroxyflavone 8-Glucopyranosylapigenin 8-Glucosylapigenin Apigenin 8-C-glucoside Orientoside C21H20O10 432.3775 432.10564686 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one vitexin 3681-93-4 OCC1OC(C(O)C(O)C1O)C1=C(O)C=C(O)C2=C1OC(=CC2=O)C1=CC=C(O)C=C1 InChI=1S/C21H20O10/c22-7-14-17(27)18(28)19(29)21(31-14)16-11(25)5-10(24)15-12(26)6-13(30-20(15)16)8-1-3-9(23)4-2-8/h1-6,14,17-19,21-25,27-29H,7H2 SGEWCQFRYRRZDC-UHFFFAOYSA-N belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Flavonoid 8-C-glycosides Organic compounds Phenylpropanoids and polyketides Flavonoids Flavonoid glycosides Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Benzene and substituted derivatives C-glycosyl compounds Chromones Dialkyl ethers Flavones Heteroaromatic compounds Hexoses Hydrocarbon derivatives Organic oxides Oxacyclic compounds Oxanes Phenolic glycosides Polyols Primary alcohols Pyranones and derivatives Secondary alcohols Vinylogous acids 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 4'-hydroxyflavonoid 5-hydroxyflavonoid 7-hydroxyflavonoid Alcohol Aromatic heteropolycyclic compound Benzenoid Benzopyran C-glycosyl compound Chromone Dialkyl ether Ether Flavone Flavonoid-8-c-glycoside Glycosyl compound Heteroaromatic compound Hexose monosaccharide Hydrocarbon derivative Hydroxyflavonoid Monocyclic benzene moiety Monosaccharide Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Phenol Phenolic glycoside Polyol Primary alcohol Pyran Pyranone Secondary alcohol Vinylogous acid logp 0.36 ALOGPS logs -2.40 ALOGPS solubility 1.73e+00 g/l ALOGPS logp -0.051 ChemAxon pka_strongest_acidic 6.17 ChemAxon pka_strongest_basic -3 ChemAxon iupac 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one ChemAxon average_mass 432.3775 ChemAxon mono_mass 432.10564686 ChemAxon smiles OCC1OC(C(O)C(O)C1O)C1=C(O)C=C(O)C2=C1OC(=CC2=O)C1=CC=C(O)C=C1 ChemAxon formula C21H20O10 ChemAxon inchi InChI=1S/C21H20O10/c22-7-14-17(27)18(28)19(29)21(31-14)16-11(25)5-10(24)15-12(26)6-13(30-20(15)16)8-1-3-9(23)4-2-8/h1-6,14,17-19,21-25,27-29H,7H2 ChemAxon inchikey SGEWCQFRYRRZDC-UHFFFAOYSA-N ChemAxon polar_surface_area 177.14 ChemAxon refractivity 106.03 ChemAxon polarizability 41.42 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 10 ChemAxon donor_count 7 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 243788 Specdb::NmrOneD 243789 Specdb::NmrOneD 243790 Specdb::NmrOneD 243791 Specdb::NmrOneD 243792 Specdb::NmrOneD 243793 Specdb::NmrOneD 243794 Specdb::NmrOneD 243795 Specdb::NmrOneD 243796 Specdb::NmrOneD 243797 Specdb::NmrOneD 243798 Specdb::NmrOneD 243799 Specdb::NmrOneD 243800 Specdb::NmrOneD 243801 Specdb::NmrOneD 243802 Specdb::NmrOneD 243803 Specdb::NmrOneD 243804 Specdb::NmrOneD 243805 Specdb::NmrOneD 243806 Specdb::NmrOneD 243807 Specdb::MsMs 100836 Specdb::MsMs 100837 Specdb::MsMs 100838 Specdb::MsMs 166284 Specdb::MsMs 166285 Specdb::MsMs 166286 Specdb::MsMs 2226440 Specdb::MsMs 2228291 Specdb::MsMs 2228764 Specdb::MsMs 2230662 Specdb::MsMs 2231092 Specdb::MsMs 2233132 Specdb::MsMs 2233484 Specdb::MsMs 2235433 Specdb::MsMs 2246248 Specdb::MsMs 2248050 Specdb::MsMs 2256522 Specdb::MsMs 2258055 Specdb::MsMs 3051194 Specdb::MsMs 3051195 Specdb::MsMs 3051196 Specdb::MsMs 3119182 Specdb::MsMs 3119183 Specdb::MsMs 3119184 Specdb::CMs 51991 Specdb::CMs 61839 Specdb::CMs 122907 Specdb::CMs 137166 Specdb::CMs 144900 Specdb::CMs 154519 Specdb::CMs 154521 Specdb::CMs 154522 Specdb::CMs 154525 Specdb::CMs 154527 Specdb::CMs 154529 Specdb::CMs 154531 Specdb::CMs 154533 Specdb::CMs 154535 Specdb::CMs 154537 Specdb::CMs 154539 Specdb::CMs 279997 Specdb::CMs 998781 Specdb::CMs 998782 Specdb::CMs 998783 Specdb::CMs 998784 Specdb::CMs 998785 Specdb::CMs 998786 Specdb::CMs 998787 Specdb::CMs 998788 Amaranth Type 1 specific Amaranthus 3564 Annual wild rice Type 1 specific Zizania aquatica 75727 Barley Type 1 specific Hordeum vulgare 4513 Black tea Type 1 Breakfast cereal Type 2 specific Bulgur Type 2 specific Cereals and cereal products Unknown generic Cocoa bean Type 1 specific Theobroma cacao 3641 Common buckwheat Type 1 specific Fagopyrum esculentum 3617 Common oregano Type 1 specific Origanum vulgare 39352 Common pea Type 1 specific Pisum sativum 3888 Common salsify Type 1 specific Tragopogon porrifolius 13731 Common wheat Type 1 specific Triticum aestivum 4565 Corn Type 1 specific Zea mays 4577 Cucumber Type 1 specific Cucumis sativus 3659 Fenugreek Type 1 specific Trigonella foenum-graecum 78534 Flaxseed Type 1 specific Linum usitatissimum 4006 Flour Type 2 specific Gram bean Type 1 specific Vigna mungo 3915 Green tea Type 1 Hard wheat Type 1 specific Triticum durum 4567 Herbal tea Type 1 Millet Type 1 specific Panicum miliaceum 4540 Mung bean Type 1 specific Vigna radiata 157791 Oat Type 1 specific Avena sativa 4498 Oriental wheat Type 1 specific Triticum turanicum 376534 Prairie turnip Type 1 specific Pediomelum esculentum 458363 Quinoa Type 1 specific Chenopodium quinoa 63459 Red rice Type 1 specific Oryza rufipogon 4529 Red tea Type 1 Rice Type 1 specific Oryza sativa 4530 Rye Type 1 specific Secale cereale 4550 Sorghum Type 1 specific Sorghum bicolor 4558 Sorrel Type 1 specific Rumex acetosa 41241 Soy bean Type 1 specific Glycine max 3847 Spelt Type 1 specific Triticum spelta 58933 Sweet marjoram Type 1 specific Origanum majorana 268884 Tamarind Type 1 specific Tamarindus indica 58860 Tartary buckwheat Type 1 specific Fagopyrum tataricum 62330 Tea Type 1 specific Camellia sinensis 4442 Teff Type 1 specific Eragrostis tef 110835 Tree fern Type 1 specific Cyathea Triticale Type 1 specific X Triticosecale rimpaui Wheat Type 1 specific Triticum 4564 Wild rice Type 1 specific Zizania 15949 Aldose reductase inhibitor 40 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21). Angiotensin converting enzyme inhibitor 18 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1). Anti dermatitic 225 A drug used to treat or prevent skin disorders or for the routine care of skin. Anti histaminic 331 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists. Anti-arrhythmic 129 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. Anti-bradiquinic 149 Anti-inflammatory 370 A substance that reduces or suppresses inflammation. Anti-oxidant 502 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. Anti-serotoninic 609 Anti-thyroid 654 Aphidifuge 701 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. cAMP-phosphodiesterase inhibitor 753 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Cancer preventive 754 A substance that inhibits or prevents the proliferation of neoplasms. Goitrogenic 959 Hypotensive 1021 Platelet aggregation inhibitor 1434 A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. Thyroid-peroxidase inhibitor 1357 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.