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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H22O10
Molecular Weight 446.4041
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GLYCITIN

SMILES

COC1=CC2=C(OC=C(C2=O)C3=CC=C(O)C=C3)C=C1O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O

InChI

InChIKey=OZBAVEKZGSOMOJ-MIUGBVLSSA-N
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/s1

HIDE SMILES / InChI

Molecular Formula C22H22O10
Molecular Weight 446.4041
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Glycitin (4'-Hydroxy-6-Methoxyisoflavone-7-D-Glucoside) is a soy isoflavone. Isoflavone mixtures from soybean containing glycitin exert anti-obese and antidiabetic, antineoplastic, antioxidant effects. Isoflavone supplementation in healthy males may enhance cognitive processes which appear dependent on oestrogen activation. Glycitin underwent hydrolysis of the beta-glycoside moiety and little further biotransformation, leading to high plasma glycitein concentrations.

CNS Activity

Curator's Comment: Soya isoflavone supplementation containing Glycitin enhances spatial working memory in men. Volunteers were randomised to take four capsules/d containing soya isoflavones (116 mg isoflavone equivalents/d: 68 mg daidzein, 12 mg genistein, 36 mg glycitin) or placebo for 6 weeks, and the alternate treatment during the following 6 weeks. Assessments of memory (verbal episodic, auditory and working), executive function (planning, attention, mental flexibility) and visual-spatial processing were performed at baseline and after each treatment period. Isoflavone supplementation significantly improved spatial working memory (P = 0.01), a test in which females consistently perform better than males. Compared with placebo supplementation, there were 18 % fewer attempts (P = 0.01), 23 % fewer errors (P = 0.02) and 17 % less time (P = 0.03) required to correctly identify the requisite information.

Originator

Sources: Kudou, S., Fleury, Y., Welti, D.. Magnoiato, D., Uchida, T., Kitamura, K., Okubo, K. Malonyl isoflavones glycosides in soybean seeds (Glycine max Merrill). Agric. Biol. Chem. 1991,55,2227-2233.
Curator's Comment: Kudou et al. (1991) isolated and characterized nine beta-glucoside forms of isoflavones from soybean hypocotyl. They are daidzin, glycitin, genistin, 6'-0-acetyl daidzin, 6'-0-acetyl glycitin, 6'-0-acetyl genistin, 6'-0-malonyl daidzin, 6'-0-malonyl glycitin and 6'-0-malonyl genistin. reference retrieved from http://lib.dr.iastate.edu/cgi/viewcontent.cgi?article=13527&context=rtd

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
200 ng/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GLYCITIN plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
36 mg 1 times / day steady, oral
Studied dose
Dose: 36 mg, 1 times / day
Route: oral
Route: steady
Dose: 36 mg, 1 times / day
Sources:
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
26.3 mg/day steady, oral
Studied dose
Dose: 26.3 mg/day
Route: oral
Route: steady
Dose: 26.3 mg/day
Sources:
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
Soy Isoflavone Glycitin (4'-Hydroxy-6-Methoxyisoflavone-7-D-Glucoside) Promotes Human Dermal Fibroblast Cell Proliferation and Migration via TGF-β Signaling.
2015-05
Soya isoflavone supplementation enhances spatial working memory in men.
2009-11
Flavonoids possess neuroprotective effects on cultured pheochromocytoma PC12 cells: a comparison of different flavonoids in activating estrogenic effect and in preventing beta-amyloid-induced cell death.
2007-03-21
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006-11
Bioavailability of pure isoflavones in healthy humans and analysis of commercial soy isoflavone supplements.
2001-04
Patents

Patents

Sample Use Guides

Volunteers were randomised to take four capsules/d containing soya isoflavones (116 mg isoflavone equivalents/d: 68 mg daidzein, 12 mg genistein, 36 mg glycitin) or placebo for 6 weeks, and the alternate treatment during the following 6 weeks. Assessments of memory (verbal episodic, auditory and working), executive function (planning, attention, mental flexibility) and visual-spatial processing were performed at baseline and after each treatment period. Glycitin (25 mg), the β-glycoside of glycitein, was administered orally as a single-bolus dose, and blood samples were collected.
Route of Administration: Oral
Treatment of primary dermal fibroblasts with glycitin increased cell proliferation and migration. In addition, treatment with 20 μM glycitin for 24 h induced the synthesis of collagen type I and type III at both the mRNA and protein levels. Fibronectin was also increased by 20% after treatment. Matrix metalloproteinase-1 collagenase was decreased in the media after 24-h incubation with glycitin, and the synthesis of transforming growth factor-beta (TGF-β) mRNA increased approximately twofold in cells following glycitin treatment. Phosphorylation of Smad2 and Smad3 increased after 1 h of glycitin treatment, and phosphorylation continued for 24 h. Furthermore, the phosphorylated form of AKT was increased in glycitin-treated cells after 3 h and remained higher for 24 h.
Substance Class Chemical
Created
by admin
on Mon Mar 31 22:54:21 GMT 2025
Edited
by admin
on Mon Mar 31 22:54:21 GMT 2025
Record UNII
G2S44P62XC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4H-1-BENZOPYRAN-4-ONE, 7-(.BETA.-D-GLUCOPYRANOSYLOXY)-3-(4-HYDROXYPHENYL)-6-METHOXY-
Preferred Name English
GLYCITIN
USP-RS  
Common Name English
3-(4-HYDROXYPHENYL)-6-METHOXY-4-OXO-4H-CHROMEN-7-YL .BETA.-D-GLUCOPYRANOSIDE
Systematic Name English
GLYCITEIN-7-.BETA.-O-GLUCOSIDE
Common Name English
GLYCITEIN 7-O-GLUCOSIDE
Common Name English
GLYCITIN [USP-RS]
Common Name English
GLYCITEIN 7-O-.BETA.-GLUCOSIDE
Common Name English
GLYCITIN (CONSTITUENT OF SOY ISOFLAVONES) [DSC]
Common Name English
Classification Tree Code System Code
DSLD 1428 (Number of products:4)
Created by admin on Mon Mar 31 22:54:21 GMT 2025 , Edited by admin on Mon Mar 31 22:54:21 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID80193227
Created by admin on Mon Mar 31 22:54:21 GMT 2025 , Edited by admin on Mon Mar 31 22:54:21 GMT 2025
PRIMARY
PUBCHEM
187808
Created by admin on Mon Mar 31 22:54:21 GMT 2025 , Edited by admin on Mon Mar 31 22:54:21 GMT 2025
PRIMARY
FDA UNII
G2S44P62XC
Created by admin on Mon Mar 31 22:54:21 GMT 2025 , Edited by admin on Mon Mar 31 22:54:21 GMT 2025
PRIMARY
WIKIPEDIA
Glycitin
Created by admin on Mon Mar 31 22:54:21 GMT 2025 , Edited by admin on Mon Mar 31 22:54:21 GMT 2025
PRIMARY
CAS
40246-10-4
Created by admin on Mon Mar 31 22:54:21 GMT 2025 , Edited by admin on Mon Mar 31 22:54:21 GMT 2025
PRIMARY
RS_ITEM_NUM
1295855
Created by admin on Mon Mar 31 22:54:21 GMT 2025 , Edited by admin on Mon Mar 31 22:54:21 GMT 2025
PRIMARY
CHEBI
80373
Created by admin on Mon Mar 31 22:54:21 GMT 2025 , Edited by admin on Mon Mar 31 22:54:21 GMT 2025
PRIMARY