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552-58-9 Usage

Description

ERIODICTYOL, a tetrahydroxyflavanone, is a flavanone with hydroxy groups substituted at positions 5, 7, 3', and 4' respectively. It is a natural compound derived from Yerba santa, an herb with medicinal properties.

Uses

Used in Biological Studies:
ERIODICTYOL is used as a source of new bifunctional scaffolds targeting cholinesterases and beta-amyloid aggregation in biological studies.
Used in Respiratory Medicine:
ERIODICTYOL is used as an ingredient in medicines for respiratory conditions such as coughs, colds, tuberculosis, asthma, and chronic bronchitis.
Used in General Health:
ERIODICTYOL is used as a remedy for fever and dry mouth. It is also utilized to relieve muscle spasms, loosen phlegm, and act as a tonic.
Used in Pharmaceutical Industry:
ERIODICTYOL is used as a natural compound in the development of new drugs and therapies, particularly for respiratory and general health applications.

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).

Check Digit Verification of cas no

The CAS Registry Mumber 552-58-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 2 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 552-58:
(5*5)+(4*5)+(3*2)+(2*5)+(1*8)=69
69 % 10 = 9
So 552-58-9 is a valid CAS Registry Number.
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

552-58-9 Well-known Company Product Price

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  • Sigma

  • (74565)  Eriodictyol  ≥95.0% (HPLC)

  • 552-58-9

  • 74565-1MG-F

  • 655.20CNY

  • Detail
  • Sigma

  • (74565)  Eriodictyol  ≥95.0% (HPLC)

  • 552-58-9

  • 74565-5MG-F

  • 1,288.17CNY

  • Detail
  • Sigma-Aldrich

  • (89061)  Eriodictyol  analytical standard

  • 552-58-9

  • 89061-10MG

  • 3,457.35CNY

  • Detail

552-58-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name eriodictyol

1.2 Other means of identification

Product number -
Other names ERIODICTYOL

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:552-58-9 SDS

552-58-9Synthetic route

eriodictyol
552-58-9

eriodictyol

Conditions
ConditionsYield
With C9H8IO4Pol In dimethyl sulfoxide at 25℃; for 2h;98%
2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

eriodictyol
552-58-9

eriodictyol

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 48h;41%
taxifolin
480-18-2

taxifolin

eriodictyol
552-58-9

eriodictyol

Conditions
ConditionsYield
With benzophenone In ethyl acetate for 24h; Irradiation; Yield given;
eriodictyol 5-O-β-D-glucoside

eriodictyol 5-O-β-D-glucoside

eriodictyol
552-58-9

eriodictyol

Conditions
ConditionsYield
acid and enzymatic hydrolysis;
5,7,3',4'-tetrahydroxyflavan-5-O-β-glucosyl-(4,8)-eridictyol

5,7,3',4'-tetrahydroxyflavan-5-O-β-glucosyl-(4,8)-eridictyol

A

eriodictyol
552-58-9

eriodictyol

B

luteolinidin

luteolinidin

Conditions
ConditionsYield
With trifluoroacetic acid at 90℃; for 0.5h;
(2R)-2r-<3,4-dihydroxy-phenyl>-3t,5,7-trihydroxy-chroman-4-one

(2R)-2r-<3,4-dihydroxy-phenyl>-3t,5,7-trihydroxy-chroman-4-one

eriodictyol
552-58-9

eriodictyol

Conditions
ConditionsYield
With hydrogenchloride; methanol; zinc
naringenin
480-41-1

naringenin

eriodictyol
552-58-9

eriodictyol

Conditions
ConditionsYield
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
1573206-81-1

(2S)-6,8-di[(1S)-(2'-O-β-D-glucopyranosyl-4'-hydroxyphenyl)-3-(4"-hydroxyphenyl)propyl]-3'-O-β-D-glucopyranosyleryodyctiol

eriodictyol
552-58-9

eriodictyol

Conditions
ConditionsYield
With hydrogenchloride; water for 1h; Reflux;
hesperidin
520-26-3

hesperidin

eriodictyol
552-58-9

eriodictyol

Conditions
ConditionsYield
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

hesperetin

eriodictyol
552-58-9

eriodictyol

Conditions
ConditionsYield
With pyridine; hydrogenchloride; aluminum (III) chloride In water at 70℃;
(S)-eriodictyol-7-O-(6′′-O-malonyl)-β-D-glucopyranoside

(S)-eriodictyol-7-O-(6′′-O-malonyl)-β-D-glucopyranoside

A

D-glucose
50-99-7

D-glucose

B

eriodictyol
552-58-9

eriodictyol

Conditions
ConditionsYield
With trifluoroacetic acid at 110℃; for 2h;
(S)-eryodictyol-7-O-(4′′-O-malonyl)-β-D-glucopyranoside

(S)-eryodictyol-7-O-(4′′-O-malonyl)-β-D-glucopyranoside

A

D-glucose
50-99-7

D-glucose

B

eriodictyol
552-58-9

eriodictyol

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

A

7-methoxy-3',4',5-trihydroxyflavanone
93012-86-3

7-methoxy-3',4',5-trihydroxyflavanone

B

eriodictyol
552-58-9

eriodictyol

C

7-methoxyflavanone
21785-09-1

7-methoxyflavanone

D

naringenin
480-41-1

naringenin

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

A

eriodictyol
552-58-9

eriodictyol

B

naringenin
480-41-1

naringenin

Conditions
ConditionsYield
With cytochromes P450 in human liver microsomes Kinetics; Enzymatic reaction;
dimethylallyl diphosphate
358-72-5

dimethylallyl diphosphate

eriodictyol
552-58-9

eriodictyol

(S)-5,7,3',4'-tetrahydroxy-8-(3',3'-dimethylallyl)flavanone

(S)-5,7,3',4'-tetrahydroxy-8-(3',3'-dimethylallyl)flavanone

Conditions
ConditionsYield
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

eriodictyol

Beauveria bassiana AM 278 grown on a sabouraud medium

Beauveria bassiana AM 278 grown on a sabouraud medium

eriodictyol 7-O-β-D-(4''-O-methyl)glucopyranoside

eriodictyol 7-O-β-D-(4''-O-methyl)glucopyranoside

Conditions
ConditionsYield
In dimethyl sulfoxide for 168h; Microbiological reaction; regioselective reaction;36%
eriodictyol
552-58-9

eriodictyol

3,3-dimethylallyl diphosphate triammonium salt
1186-30-7, 45126-99-6, 69382-61-2

3,3-dimethylallyl diphosphate triammonium salt

A

C25H28O6

C25H28O6

B

5′-prenyleriodictyol
87746-47-2

5′-prenyleriodictyol

C

(S)-5,7,3',4'-tetrahydroxy-6-(3',3'-dimethylallyl)flavanone

(S)-5,7,3',4'-tetrahydroxy-6-(3',3'-dimethylallyl)flavanone

Conditions
ConditionsYield
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

eriodictyol

Absidia coerulea AM 93 grown on a sabouraud medium

Absidia coerulea AM 93 grown on a sabouraud medium

pyracanthoside

pyracanthoside

Conditions
ConditionsYield
In dimethyl sulfoxide for 168h; Microbiological reaction; regioselective reaction;30%
eriodictyol
552-58-9

eriodictyol

6-bromoeriodictyol

6-bromoeriodictyol

eriodictyol
552-58-9

eriodictyol

(2S)-luteoforol

(2S)-luteoforol

Conditions
ConditionsYield
With borohydride
eriodictyol
552-58-9

eriodictyol

AdoMet

AdoMet

Conditions
ConditionsYield
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

eriodictyol

C15H10O6

C15H10O6

Conditions
ConditionsYield
With 2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl In methanol at 22℃; Kinetics; Further Variations:; reagents ratio;
eriodictyol
552-58-9

eriodictyol

4',5,7-tetrahydroxyflavylium
16975-93-2

4',5,7-tetrahydroxyflavylium

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: borohydride
2: 2M HCl / 0.25 h / Heating
View Scheme
eriodictyol
552-58-9

eriodictyol

C15H10O6(1-)

C15H10O6(1-)

Conditions
ConditionsYield
With potassium dihydrogenphosphate; sodium riboflavin-5'-monophosphate; sodium hydroxide In water; acetonitrile pH=7; Inert atmosphere; UV-irradiation;
eriodictyol
552-58-9

eriodictyol

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on
491-70-3

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Conditions
ConditionsYield
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

eriodictyol

orobol
480-23-9

orobol

Conditions
ConditionsYield
With NADPH disodium salt; D-Galactose In dimethyl sulfoxide at 30℃; for 72h; Microbiological reaction;
eriodictyol
552-58-9

eriodictyol

eriodictoyl dihydrochalcone
57765-66-9

eriodictoyl dihydrochalcone

Conditions
ConditionsYield
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

eriodictyol

C23H24O6

C23H24O6

Conditions
ConditionsYield
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

eriodictyol

C28H32O6

C28H32O6

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

552-58-9Relevant articles and documents

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

Campana, Priscilla R. V.,Coleman, Christina M.,Teixeira, Mauro M.,Ferreira, Daneel,Braga, Fern?o C.

, p. 824 - 830 (2014)

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

Miura, Motofumi,Shigematsu, Karin,Toriyama, Masaharu,Motohashi, Shigeyasu

, (2021/10/25)

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.

Optimization of the biosynthesis of b-ring ortho-hydroxy lated flavonoids using the 4-hydroxyphenylacetate 3-hydroxylase complex (Hpabc) of escherichia coli

Chen, Yang,Gao, Liping,Gui, Lin,Guo, Lina,Lei, Ting,Li, Yan,Ma, Xiubing,Ruan, Haixiang,Wang, Longji,Wang, Yunsheng,Xia, Tao

, (2021/05/31)

Flavonoids are important plant metabolites that exhibit a wide range of physiological and pharmaceutical functions. Because of their wide biological activities, such as anti-inflammatory, antioxidant, antiaging and anticancer, they have been widely used in foods, nutraceutical and pharmaceuticals industries. Here, the hydroxylase complex HpaBC was selected for the efficient in vivo production of ortho-hydroxylated flavonoids. Several HpaBC expression vectors were constructed, and the corresponding products were successfully detected by feeding naringenin to vector-carrying strains. However, when HpaC was linked with an S-Tag on the C terminus, the enzyme activity was significantly affected. The optimal culture conditions were determined, including a substrate concentration of 80 mg·L?1, an induction temperature of 28?C, an M9 medium, and a substrate delay time of 6 h after IPTG induction. Finally, the efficiency of eriodictyol conversion from P2&3-carrying strains fed naringin was up to 57.67 ± 3.36%. The same strategy was used to produce catechin and caf-feic acid, and the highest conversion efficiencies were 35.2 ± 3.14 and 32.93 ± 2.01%, respectively. In this paper, the catalytic activity of HpaBC on dihydrokaempferol and kaempferol was demonstrated for the first time. This study demonstrates a feasible method for efficiently synthesizing in vivo B-ring dihydroxylated flavonoids, such as catechins, flavanols, dihydroflavonols and flavonols, in a bacterial expression system.

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