Tectorigenin Chemical Properties

Melting point:

225-226°

Boiling point:

361.5°C (rough estimate)

Density 

1.512

refractive index 

1.4600 (estimate)

storage temp. 

Sealed in dry,2-8°C

solubility 

DMSO : 150 mg/mL (499.57 mM; Need ultrasonic and warming)

form 

powder to crystal

pka

6.49±0.20(Predicted)

color 

White to Orange to Green

BRN 

305601

InChI

InChI=1S/C16H12O6/c1-21-16-11(18)6-12-13(15(16)20)14(19)10(7-22-12)8-2-4-9(17)5-3-8/h2-7,17-18,20H,1H3

InChIKey

OBBCRPUNCUPUOS-UHFFFAOYSA-N

SMILES

C1OC2=CC(O)=C(OC)C(O)=C2C(=O)C=1C1=CC=C(O)C=C1

CAS DataBase Reference

548-77-6

Safety Information

WGK Germany 

3

RTECS 

NR2400000

HS Code 

2932.99.6100

Tectorigenin Usage And Synthesis

Description

Tectorigenin is an isoflavone that exists in numerous plant resources, and it is especially abundant in Belamcandae Rhizoma and Puerariae flos, which both have the effects of clearing away heat, removing toxic substances, relieving sore throat, and reducing swelling. As one of the most important active ingredients, the pharmacological effects of tectorigenin have been demonstrated by an increasing number of investigators. Due to its extensive pharmacological activities, including anticancer, antioxidation, hepatoprotection, anti-inflammation, etc., tectorigenin has received a large amount of attention[1].

Occurrence

Tectorigenin, a methoxy isoflavone with three hydroxyl groups, is chemically noted as 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one. As a bioactive compound, tectorigenin is found in several plant species, most notably in the rhizomes of Belamcanda chinensis (L.) DC., a traditional Chinese medicine (TCM) named Belamcandae Rhizoma. The Iris family is the major source of tectorigenin, and many Iridaceous plants, such as Iris spuria L. (Calizona), Iris tectorum Maxim, Iris japonica Thunb., Iris dichotoma Pall., Iris germanica L., Iris unguicularis Poiret, Iris loczyi Kan., Iris kashmiriana Baker, Iris crocea Jacq. ex R. C. Foster, Iris ensata Thunb., Iris germanica L., Iris hungarica Waldst. et Kit., Iris confusa Sealy, and Iris pseudacorus L. contain abundant tectorigenin, so tectorigenin is also known as iris flavone. Tectorigenin also exists in some leguminous plants, such as the flowers of Pueraria lobata (Willd.) Ohwi, Pueraria thomsonii Benth., and Pueraria thunbergiana Benth. are also TCM called Puerariae Flos. Tectorigenin was isolated from the leaves of Dalbergia odorifera T. Chen, the heartwood of Dalbergia parviflora Roxb., and the roots of Euchresta formosana (Hayata) Ohwi as well. Moreover, some plants in other families also contain tectorigenin, including Codonopsis pilosula (Franch.) Nannf. (Campanulaceae), Morus alba L. (Moraceae), Viola hondoensis W. Becker et H. Boissieu. (Violaceae), and Eleocharis dulcis (Burm. f.) Trin. ex Hensch. (Cyperaceae)[1].

Uses

Tectorigenin is identified as an α-glucosidase inhibitors. Potent lactate dehydrogenase (LDH) inhibitor.

Definition

ChEBI: A methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 5, 7 and 4' respectively.

Synthesis Reference(s)

Synthetic Communications, 38, p. 525, 2008 DOI: 10.1080/00397910701796725

References

[1] Juan Rong. “Tectorigenin: A Review of Its Sources, Pharmacology, Toxicity, and Pharmacokinetics.” Molecules 28 15 (2023).

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