5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Base Information

• Chemical Name: 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
• CAS No.: 69097-99-0
• Molecular Formula: C₁₆H₁₄O₆
• Molecular Weight: 302.284
• Hs Code.: 2932990090
• NSC Number: 641520,57654
• DSSTox Substance ID: DTXSID80274404,DTXSID70859446
• Nikkaji Number: J294.471E
• Wikidata: Q27166968
• ChEMBL ID: CHEMBL88169
• Mol file: 69097-99-0.mol

Synonyms:69097-99-0;rac-Hesperetin;(Rac)-Hesperetin;(R)-Hesperetin;(+/-)-Hesperetin;5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one;NSC641520;5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one;MLS002667896;5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one;(2S)-5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-chromanone, 3',5,7-Trihydroxy-4-methoxyflavanone;hesperetine;5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-chromanone;Hersperatine;MFCD00075646;Hesperetin, >=95%;CHEMBL88169;SCHEMBL765368;Hesperetin, analytical standard;ACon1_002327;CHEBI:95167;HY-N0168A;DTXSID70859446;DTXSID80274404;HMS3373J01;HMS3656C03;NSC57654;3',7-Trihydroxy-4'-methoxyflavanone;5,3'-Trihydroxy-4'-methoxyflavanone;AKOS015995360;(+/-)-Hesperetin, analytical standard;Flavanone,5,7-trihydroxy-4'-methoxy-;NSC-641520;NCGC00095618-01;NCGC00095618-02;AS-11672;NCI60_014043;SMR001557653;SY057338;XH167423;3/',5,7-Trihydroxy-4/'-methoxyflavanone;CS-0111125;FT-0626940;EN300-23521574;BRD-A44482398-001-01-3;Q27166968;FE387278-0643-4EBB-902D-C81B1FCDE1F8;5,7-dihydroxy-2-(3-hydroxy-4-methoxy-phenyl)chroman-4-one;5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-chromen-4-one;4H-1-Benzopyran-4-one,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (S)-;5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one

Chemical Property of 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Chemical Property:

• Melting Point: 227-232°C
• Boiling Point: 586.2±50.0 °C(Predicted)
• PKA: 7.49±0.40(Predicted)
• PSA: 96.22000
• Density: 1.458±0.06 g/cm3(Predicted)
• LogP: 2.51850
• Storage Temp.: 2-8°C
• Solubility.: ethanol: soluble50mg/mL, clear to almost clear, colorless to sli
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 302.07903816
• Heavy Atom Count: 22
• Complexity: 413

Purity/Quality:

98%,99%, ^*data from raw suppliers

rac-Hesperetin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2CC(=O)C3=C(C=C(C=C3O2)O)O)O
• Uses: Hesperetin has been used as a standard in studies involving the cytotoxic effect of hesperetin on doxorubicin-resistant MCF-7 cells using enzyme-linked immunosorbent assay (ELISA) technique.

Technology Process of 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

There total 38 articles about 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 28.0%

7-hydroxy-4-methyl-chromen-2-one (90-33-5,79566-13-5) + hesperidin (520-26-3) → 4-methylumbelliferyl-rutinoside (1356391-89-3) + hesperetin (520-33-2,41001-90-5,69097-99-0)

Guidance literature:

With water; In dimethyl sulfoxide; at 30 ℃; for 1h; pH=5; aq. buffer; Enzymatic reaction;

DOI:10.1016/j.carres.2011.11.008

Reference yield: 3.5%

hesperidin (520-26-3) → hesperetin (520-33-2,41001-90-5,69097-99-0) + 3′,5,7,8-tetrahydroxy-4′-methoxyflavanone

Guidance literature:

With Aspergillus saitoi; In water; dimethyl sulfoxide; at 30 ℃; pH=5.0;

DOI:10.1271/bbb.67.1443

Reference yield:

hesperetin 7‐O‐β‐D‐glucopyranoside → β-D-glucose (492-61-5) + hesperetin (520-33-2,41001-90-5,69097-99-0)

Guidance literature:

With water; Enzymatic reaction;

DOI:10.1016/j.carres.2011.11.008

upstream raw materials:

hesperidin

4^G-α-D-glucopyranosyl hesperidin

(S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-benzopyrone

methanol

Downstream raw materials:

5-hydroxy-3′4′7-trimethoxy flavanone

(S)-5,7-diacetoxy-2-(3-acetoxy-4-methoxy-phenyl)-chroman-4-one

(-)-hesperetin oxime

5-hydroxy-6,3',4'-trimethoxyflavanone

Refernces

• 1、 Zheng, Yan,Zhang, Yi-long,Li, Zeng,Shi, Wen,Ji, Ya-ru,Guo, Ya-Hui,Huang, Cheng,Sun, Guo-ping,Li, Jun. "Design and synthesis of 7-O-1,2,3-triazole hesperetin derivatives to relieve inflammation of acute liver injury in mice". . . Retrieved 2021/01/25.
• 2、 dos Santos, Roney Vander,Grillo, Giovanna,Fonseca, Henrique,Stanisic, Danijela,Tasic, Ljubica. "Hesperetin as an inhibitor of the snake venom serine protease from Bothrops jararaca". . p. 64 - 72. Retrieved 2021/05/13.