552-58-9

Basic information

• Product Name: ERIODICTYOL
• Synonyms: (S)-3',4',5,7-TETRAHYDROXYFLAVANONE;ERIODICTYOL;5,7,3',4'-TETRAHYDROXYFLAVANONE;2-[3,4-DIHYDROXYPHENYL]2,3-DIHYDRO-5,7-DIHYDROXY-4H-1BENZOPYRAN-4-ONE;3',4',5,7-TETRAHYDROXYFLAVANONE;(S)-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4-benzopyrone;(2S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-chroman-4-one;ERIODICTYOL(SH)
• CAS NO: 552-58-9
• Molecular Formula: C₁₅H₁₂O₆
• Molecular Weight: 288.25
• EINECS: 209-016-4
• Product Categories: Flavanones;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 552-58-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 270°C
• Boiling Point: 625.2 °C at 760 mmHg
• Flash Point: 241.9 °C
• Appearance: Needle crystalline powder
• Density: 1.586 g/cm³
• Vapor Pressure: 3.19E-16mmHg at 25°C
• Refractive Index: 1.724
• Storage Temp.: ?20°C
• Solubility: DMSO (Slightly), Methanol (Very Slightly)
• PKA: 7.49±0.40(Predicted)
• Water Solubility: 70mg/L(20 oC)
• Stability: Hygroscopic
• BRN: 5104930
• CAS DataBase Reference: ERIODICTYOL(CAS DataBase Reference)
• NIST Chemistry Reference: ERIODICTYOL(552-58-9)
• EPA Substance Registry System: ERIODICTYOL(552-58-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 552-58-9(Hazardous Substances Data)

Usage

Uses

Eriodictyol is used in biological studies as natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation. Eriodictyl is extracted from Yerba santa, an herb. The leaf is used to make medicine.Yerba santa is used for respiratory conditions including coughs, colds, tuberculosis, asthma, and chronic bronchitis. It is also used for fever and dry mouth. Some people use it to relieve muscle spasms, to loosen phlegm, and as a tonic.

Definition

ChEBI: A tetrahydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 7, 3' and 4' respectively.

Biochem/physiol Actions

The flavanone eriodictyol is a metabolite in the flavonoid biosynthesis pathway. Eriodictyol has anti-inflammatory and antioxidant activities and taste-modifying properties; it is extracted from plants such as Eriodictyon californicum, the twigs of Millettia duchesnei, in Eupatorium arnottianum, lemons and as glycoside in rose hips (Rosa canina).

InChI:InChI=1/C15H12O6/c16-8-4-11(19)15-12(20)6-13(21-14(15)5-8)7-1-2-9(17)10(18)3-7/h1-5,13,16-19H,6H2

Synthetic route

homoeriodictyol (446-71-9, 69097-98-9, 107657-60-3) → eriodictyol (552-58-9)

Conditions	Yield
With C9H8IO4Pol In dimethyl sulfoxide at 25℃; for 2h;	98%

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on (491-70-3) → eriodictyol (552-58-9)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 48h;	41%

taxifolin (480-18-2) → eriodictyol (552-58-9)

Conditions	Yield
With benzophenone In ethyl acetate for 24h; Irradiation; Yield given;

eriodictyol 5-O-β-D-glucoside → eriodictyol (552-58-9)

Conditions	Yield
acid and enzymatic hydrolysis;

5,7,3',4'-tetrahydroxyflavan-5-O-β-glucosyl-(4,8)-eridictyol → eriodictyol (552-58-9) + luteolinidin

Conditions	Yield
With trifluoroacetic acid at 90℃; for 0.5h;

(2R)-2r-<3,4-dihydroxy-phenyl>-3t,5,7-trihydroxy-chroman-4-one → eriodictyol (552-58-9)

Conditions	Yield
With hydrogenchloride; methanol; zinc

naringenin (480-41-1) → eriodictyol (552-58-9)

Conditions	Yield
With mutant Q87W T115A H132L R191W G294D actinomycete cytochrome P450; water at 28℃; for 3h; pH=7.4; aq. phosphate buffer; Enzymatic reaction;
With cytochromes P450 in human liver microsomes Kinetics; Enzymatic reaction;

(2S)-6,8-di[(1S)-(2'-O-β-D-glucopyranosyl-4'-hydroxyphenyl)-3-(4"-hydroxyphenyl)propyl]-3'-O-β-D-glucopyranosyleryodyctiol (1573206-81-1) → eriodictyol (552-58-9)

Conditions	Yield
With hydrogenchloride; water for 1h; Reflux;

hesperidin (520-26-3) → eriodictyol (552-58-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / ethanol / 60 °C 2: pyridine; aluminum (III) chloride; hydrogenchloride / water / 70 °C View Scheme

hesperetin (520-33-2) → eriodictyol (552-58-9)

Conditions	Yield
With pyridine; hydrogenchloride; aluminum (III) chloride In water at 70℃;

(S)-eriodictyol-7-O-(6′′-O-malonyl)-β-D-glucopyranoside → D-glucose (50-99-7) + eriodictyol (552-58-9)

Conditions	Yield
With trifluoroacetic acid at 110℃; for 2h;

(S)-eryodictyol-7-O-(4′′-O-malonyl)-β-D-glucopyranoside → D-glucose (50-99-7) + eriodictyol (552-58-9)

Conditions	Yield
With trifluoroacetic acid at 110℃; for 2h;

(-)-(S)-sakuranetin (520-29-6, 2957-21-3, 17784-36-0, 118244-13-6) → eriodictyol (552-58-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: cytochromes P450 in human liver microsomes / Enzymatic reaction 2: cytochromes P450 in human liver microsomes / Enzymatic reaction View Scheme
Multi-step reaction with 2 steps 1: cytochromes P450 in human liver microsomes / Enzymatic reaction 2: cytochromes P450 in human liver microsomes / Enzymatic reaction View Scheme

(-)-(S)-sakuranetin (520-29-6, 2957-21-3, 17784-36-0, 118244-13-6) → 7-methoxy-3',4',5-trihydroxyflavanone (93012-86-3) + eriodictyol (552-58-9) + 7-methoxyflavanone (21785-09-1) + naringenin (480-41-1)

Conditions	Yield
With cytochromes P450 in human liver microsomes Kinetics; Enzymatic reaction;

(-)-(S)-sakuranetin (520-29-6, 2957-21-3, 17784-36-0, 118244-13-6) → eriodictyol (552-58-9) + naringenin (480-41-1)

Conditions	Yield
With cytochromes P450 in human liver microsomes Kinetics; Enzymatic reaction;

dimethylallyl diphosphate (358-72-5) + eriodictyol (552-58-9) → (S)-5,7,3',4'-tetrahydroxy-8-(3',3'-dimethylallyl)flavanone

Conditions	Yield
With recombinant Sophora flavescens flavonoid prenyltransferase; magnesium chloride In aq. buffer at 40℃; for 2h; pH=9; Kinetics; Enzymatic reaction; stereospecific reaction;	63.4%

eriodictyol (552-58-9) + Beauveria bassiana AM 278 grown on a sabouraud medium → eriodictyol 7-O-β-D-(4''-O-methyl)glucopyranoside

Conditions	Yield
In dimethyl sulfoxide for 168h; Microbiological reaction; regioselective reaction;	36%

eriodictyol (552-58-9) + 3,3-dimethylallyl diphosphate triammonium salt (1186-30-7, 45126-99-6, 69382-61-2) → C25H28O6 + 5′-prenyleriodictyol (87746-47-2) + (S)-5,7,3',4'-tetrahydroxy-6-(3',3'-dimethylallyl)flavanone

Conditions	Yield
With indole prenyltransferase 7-DMATS; calcium chloride In dimethyl sulfoxide; glycerol at 37℃; for 16h; pH=7.5; Kinetics; Time; Enzymatic reaction;	A 23.9% B 31.1% C 22.8%

eriodictyol (552-58-9) + Absidia coerulea AM 93 grown on a sabouraud medium → pyracanthoside

Conditions	Yield
In dimethyl sulfoxide for 168h; Microbiological reaction; regioselective reaction;	30%

eriodictyol (552-58-9) → 6-bromoeriodictyol

eriodictyol (552-58-9) → (2S)-luteoforol

Conditions	Yield
With borohydride

eriodictyol (552-58-9) + AdoMet → homoeriodictyol (446-71-9, 69097-98-9, 107657-60-3)

Conditions	Yield
With DL-dithiothreitol; HCl buffer; 2-amino-2-hydroxymethyl-1,3-propanediol at 37℃; for 1h; pH=7.5; Enzyme kinetics; Enzymatic reaction;
With DL-dithiothreitol; HCl buffer; 2-amino-2-hydroxymethyl-1,3-propanediol at 37℃; for 1h; pH=7.5; Enzymatic reaction;

eriodictyol (552-58-9) → C15H10O6

Conditions	Yield
With 2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl In methanol at 22℃; Kinetics; Further Variations:; reagents ratio;

eriodictyol (552-58-9) → 4',5,7-tetrahydroxyflavylium (16975-93-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: borohydride 2: 2M HCl / 0.25 h / Heating View Scheme

eriodictyol (552-58-9) → C15H10O6(1-)

Conditions	Yield
With potassium dihydrogenphosphate; sodium riboflavin-5'-monophosphate; sodium hydroxide In water; acetonitrile pH=7; Inert atmosphere; UV-irradiation;

eriodictyol (552-58-9) → 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on (491-70-3)

Conditions	Yield
With GLUTATHIONE; N-[tris(hydroxymethyl)methyl]glycine; flavone synthase II; NADPH; potassium hydroxide at 25℃; for 0.5h; pH=7.9; Enzymatic reaction;
Stage #1: eriodictyol With pyridine; iodine Stage #2: With pyrographite In ethanol at 70℃; for 0.5h;

eriodictyol (552-58-9) → orobol (480-23-9)

Conditions	Yield
With NADPH disodium salt; D-Galactose In dimethyl sulfoxide at 30℃; for 72h; Microbiological reaction;

eriodictyol (552-58-9) → eriodictoyl dihydrochalcone (57765-66-9)

Conditions	Yield
With Eubacterium ramulus DSM 16296 chalcone isomerase; Eubacterium ramulus DSM 16296 enoate reductase In aq. phosphate buffer at 23℃; for 17h; pH=7.5; Inert atmosphere; Enzymatic reaction;

eriodictyol (552-58-9) → C23H24O6

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / Heating 2: oxalic acid / Heating View Scheme

eriodictyol (552-58-9) → C28H32O6

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / Heating 2: oxalic acid / Heating View Scheme

Upstream product

• 480-18-2 taxifolin 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 314734-03-7 2'-hydroxy-3,4,4',6'-tetrakis(methoxymethoxy)chalcone 
• 6515-06-6 3,4-bis-methoxymethoxy-benzaldehyde 
• 73692-51-0 2',3,4,4',6'-pentahydroxychalcone 
• 13241-33-3 neohesperidin 
• 520-29-6 (-)-(S)-sakuranetin 
• 491-70-3 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on 
• 520-33-2 hesperetin 
• 520-26-3 hesperidin 
• 1573206-81-1 (2S)-6,8-di[(1S)-(2'-O-β-D-glucopyranosyl-4'-hydroxyphenyl)-3-(4-hydroxyphenyl)propyl]-3'-O-β-D-glucopyranosyleryodyctiol 
• 446-71-9 homoeriodictyol 
• 480-41-1 naringenin 

Downstream Products

• 10210-16-9 tertra-O-acetyleriodictyol 
• 6599-89-9 5,7,3',4'-tetrahydroxyflavanone tetraacetate 
• 16975-93-2 4',5,7-tetrahydroxyflavylium 
• 491-70-3 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on 
• 446-71-9 homoeriodictyol 
• 520-33-2 hesperetin 
• 87746-47-2 5′-prenyleriodictyol 
• 57765-66-9 eriodictoyl dihydrochalcone 
• 480-23-9 orobol 

Relevant articles and documents

TNF-α inhibition elicited by mansoins A and B, heterotrimeric flavonoids isolated from mansoa hirsuta

Mansoins A (1) and B (2) isolated from the fruits of Mansoa hirsuta represent new glucosylated heterotrimeric flavonoids with a flavanone core linked to two 1,3-diarylpropane C6-C3-C6 units. Their structures and absolute c

Convenient synthesis of flavanone derivatives via oxa-Michael addition using catalytic amount of aqueous cesium fluoride

A total of 36 flavanones, which included polycyclic aromatic and heterocyclic rings, were readily synthesized via oxa-Michael addition from the corresponding hydroxychalcones with a catalytic amount of aqueous cesium fluoride solution under mild conditions. This method could be applied to the scalable synthesis of eriodictyol as a known potent inhibitor of the SARS-CoV-2 spike protein.

Semi-synthesis method of eriodictyol

The invention relates to the field of chemical synthesis, and particularly relates to a semi-synthesis method of eriodictyol, and aims to solve the problems that raw materials are difficult to obtain, the process is complicated, the cost is high and the yield is low in the synthesis process of the eriodictyol at present. The technical scheme adopted by the invention is as follows: the semi-synthesis method of eriodictyol comprises the steps of 1) mixing neohesperidin and hydrobromic acid in a mass ratio of 1: (5-8), heating after mixing, monitoring a liquid phase until the purity of eriodictyol reaches 89-91% or above, and stopping reaction to obtain a reaction liquid; 2) adding water into the reaction liquid for cooling, and performing suction filtration to obtain a wet crude eriodictyol product; 3) adding ethanol into the wet crude eriodictyol product, and adding activated carbon for decoloration; and 4) after the decoloration is completed, removing the activated carbon, concentrating the ethanol solution dissolved with eriodictyol, standing for crystallization, and carrying out suction filtration and drying to obtain an eriodictyol refined product.