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Glycitin

Names
IUPAC name 7-(β-D-Glucopyranosyloxy)-4′-hydroxy-6-methoxyisoflavone
Systematic IUPAC name 3-(4-Hydroxyphenyl)-6-methoxy-7-{oxy}-4H-1-benzopyran-4-one
Other names Glycitein 7-O-glucoside
Identifiers
CAS Number	40246-10-4
3D model (JSmol)	Interactive image
ChEBI	CHEBI:80373
ChemSpider	163248
KEGG	C16195
PubChem CID	187808
UNII	G2S44P62XC
CompTox Dashboard (EPA)	DTXSID80193227
InChI InChI=1S/C22H22O10/c1-29-15-6-12-14(30-9-13(18(12)25)10-2-4-11(24)5-3-10)7-16(15)31-22-21(28)20(27)19(26)17(8-23)32-22/h2-7,9,17,19-24,26-28H,8H2,1H3/t17-,19-,20+,21-,22-/m1/s1Key: OZBAVEKZGSOMOJ-MIUGBVLSSA-N
SMILES COC1=C(C=C2C(=C1)C(=O)C(=CO2)C3=CC=C(C=C3)O)O4((((O4)CO)O)O)O
Properties
Chemical formula	C22H22O10
Molar mass	446.408 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Glycitin (glycitein 7-O-glucoside) is an isoflavone found in soy, and remains to various degrees in soy products like tofu, soymilk and soy sauce. Although glycitin has its own health associated properties (below), it can be transformed to glycitein by human intestinal flora by the action of beta-glucosidases.

Properties

Some interesting effects of glycitin include human dermal fibroblast cell proliferation and migration via TGF‐β signaling, glycitin treatment produces anti-photoaging effects such as collagen type I and collagen type III increase at both the mRNA and protein levels. Other noted effects decreased elastase, and decreased β‐galactosidase activation. In conjunction with 4′,6,7-trimethoxyisoflavone (TMF), an isoflavone that promotes fibroblast migration but not proliferation, wound healing and anti-scarring activity (reorganization and wound fibrosis inhibition) were significantly and synergistically boosted in both in vivo mice and in vitro.

References

1. Hsiao, Yu-Hsuan; Yu, Chia-Jung; Li, Wen-Tai; Hsieh, Jung-Feng (2015). "Coagulation of β-conglycinin, glycinin and isoflavones induced by calcium chloride in soymilk". Scientific Reports. 5: 13018. Bibcode:2015NatSR...513018H. doi:10.1038/srep13018. PMC 4542527. PMID 26260443.
2. "Health Benefits of Naturally Brewed Soy Sauce". 2018-04-04.
3. "Human Metabolome Database: Showing metabocard for Glycitin (HMDB0002219)".
4. Kim, Young Mee; Huh, Jung Sik; Lim, Yoongho; Cho, Moonjae (2015). "Soy Isoflavone Glycitin (4'-Hydroxy-6-Methoxyisoflavone-7-D-Glucoside) Promotes Human Dermal Fibroblast Cell Proliferation and Migration via TGF-β Signaling". Phytotherapy Research. 29 (5): 757–769. doi:10.1002/ptr.5313. PMID 25758427. S2CID 206430410.
5. Kim, Joungmok; Yang, Goowon; Kim, Yeji; Kim, Jin; Ha, Joohun (2016). "AMPK activators: Mechanisms of action and physiological activities". Experimental & Molecular Medicine. 48 (4): e224. doi:10.1038/emm.2016.16. PMC 4855276. PMID 27034026.

v t e Soy (Glycine max)
General	Soy allergy Soy candle Soy ink Soy molasses Soy paint Soy protein Soybean Diseases Soybean meal Soybean oil
Soy-based dishes	List of soy-based foods Aburaage Agedashi tofu Bai ye Douhua Dubu kimchi Edamame Hiyayakko Kongguksu Kongnamul Mapo doufu Miso soup Sundubu jjigae Tahu goreng Tofu skin roll Yong tau foo
Plant milk	Soy milk Soy yogurt Vegan cheese
Meat analogues	Beanfeast Tempeh Textured vegetable protein Tofu Tofurkey Vegetarian hot dog Veggie burger
Sauces and condiments	Soy sauce based Ganjang Ponzu Sweet soy sauce Tamari Teriyaki Tsuyu Yìn yóu Pastes Doenjang Doubanjiang Miso Sweet bean sauce Yellow soybean paste Tương Fermented bean Akhuni Fermented bean curd Douchi Kinema Tauco Nattō
Other foods	Mamenori Mao tofu Oncom Soy flour Soy milk based infant formula Soy nut Soy pulp Stinky tofu Tofu skin List of fermented soy products
Biochemicals	Phytoestrogens Genistein Genistin Glycitein Glycitin Ononin Daidzein Equol (metabolite) O-DMA (metabolite) Daidzin (leaves) Globulins (proteins) Beta-conglycinin Glycinin PHAs (lectins) Soybean agglutinin (lectin) Enzymes Beta-amylase Lipoxygenase Cysteine proteases Trypsin inhibitors Kunitz inhibitor Bowman-Birk inhibitor Other Soy lecithin (mix of Phospholipids) Lunasin Unsaponifiables Tocopherols Sterols Antinutrients Phytates Protease Inhibitors Cystatins
Companies	8th Continent Alpro Boca Burger Gardenburger Kikkoman Morningstar Farms Mr Bean Plamil Foods Silk So Good Tofutti Vitasoy Yamasa Yeo Hiap Seng
Other	Diet for a Small Planet Kikkoman Soy Sauce Museum William Shurtleff and Akiko Aoyagi Yuasa, artisan town of historic soy sauce distilleries
Category: Soybeans

• Glucosides
• Isoflavones