Details
Manufacturer supply top purity 3-HYDROXYFLAVONE 577-85-5 with GMP standards
- Molecular Formula: C15H10 O3
- Molecular Weight: 238.243
- Appearance/Colour: yellow fluffy powder
- Vapor Pressure: 6.63E-07mmHg at 25°C
- Melting Point: 171-172 ºC(lit.)
- Refractive Index: 1.5740 (estimate)
- Boiling Point: 393.7 ºC at 760 mmHg
- PKA: 8.80±0.20(Predicted)
- Flash Point: 151.5 ºC
- PSA： 50.44000
- Density: 1.367 g/cm3
- LogP: 3.16560
3-HYDROXYFLAVONE(Cas 577-85-5) Usage
|
Synthesis Reference(s) |
Tetrahedron Letters, 25, p. 5561, 1984 DOI: 10.1016/S0040-4039(01)81626-9 |
|
Purification Methods |
Recrystallise it from MeOH (m 169.5-170o), EtOH, aqueous EtOH (m 167o) or hexane. It has also been purified by repeated sublimation under high vacuum, and dried at high vacuum pumping for at least one hour [Bruker & Kelly J Phys Chem 91 2856 1987]. [Beilstein 17 H 527, 17 I 268, 17 II 498, 17 III/IV 6428.] |
|
General Description |
3-Hydroxyflavone is a flavonoid derivative that exhibits potential as a mushroom tyrosinase inhibitor, which could be relevant for treating pigmentation-related disorders, and also demonstrates antimicrobial properties. Its scaffold serves as a key structure for synthesizing bioactive derivatives, with studies highlighting its role in structure-activity relationships and molecular interactions with enzymes. |
|
Definition |
ChEBI: A monohydroxyflavone that is the 3-hydroxy derivative of flavone. |
InChI:InChI=1/C15H10O3/c16-13-11-8-4-5-9-12(11)18-15(14(13)17)10-6-2-1-3-7-10/h1-9,17H
577-85-5 Relevant articles
Transient Absorption Study of the Intramolecular Excited-State and Ground-State Proton Transfer in 3-Hydroxyflavone and 3-Hydroxychromone
Itoh, Michiya,Tanimoto, Yoshifumi,Tokumura, Kunihiro
, p. 3339 - 3340 (1983)
-
REACTION OF CHROMOUS CHLORIDE WITH 3-NITROFLAVENES. A NOVEL SYNTHESIS OF FLAVONOLS
Rao, T. Sudhakara,Mathur, H. H.,Trivedi, G. K.
, p. 5561 - 5562 (1984)
Reaction of Chromium(II) chloride with 3...
Direct evidence of excited-state intramolecular proton transfer in 2'-hydroxychalcone and photooxygenation forming 3-hydroxyflavone
Chou,Matinez,Cooper
, p. 4943 - 4944 (1992)
-
An easy way for constructing hard-to-make epoxides employing HOF·CH3CN
Golan, Elizabeth,Hagooly, Aviv,Rozen, Shlomo
, p. 3397 - 3399 (2004)
HOF·CH3CN, a very efficient oxygen trans...
Proton Transfer in Matrix-Isolated 3-Hydroxyflavone and 3-Hydroxyflavone Complexes
Brucker, G. A.,Kelley, D. F.
, p. 2856 - 2861 (1987)
The proton-transfer dynamics of 3-hydrox...
Oxygenolysis of a series of copper(ii)-flavonolate adducts varying the electronic factors on supporting ligands as a mimic of quercetin 2,4-dioxygenase-like activity
Anoop, Anakuthil,Dey, Subhasis,Mandal, Sukanta,Podder, Nirmalya
supporting information, p. 4338 - 4353 (2022/04/07)
Four copper(ii)-flavonolate compounds of...
Exploring 3-hydroxyflavone scaffolds as mushroom tyrosinase inhibitors: synthesis, X-ray crystallography, antimicrobial, fluorescence behaviour, structure-activity relationship and molecular modelling studies
Ashraf, Jamshaid,Mughal, Ehsan Ullah,Sadiq, Amina,Bibi, Maryam,Naeem, Nafeesa,Ali, Anser,Massadaq, Anam,Fatima, Nighat,Javid, Asif,Zafar, Muhammad Naveed,Khan, Bilal Ahmad,Nazar, Muhammad Faizan,Mumtaz, Amara,Tahir, Muhammad Nawaz,Mirzaei, Masoud
, p. 7107 - 7122 (2020/08/21)
To explore new scaffolds as tyrosinase e...
Synthesis, inverse docking-assisted identification and in vitro biological characterization of Flavonol-based analogs of fisetin as c-Kit, CDK2 and mTOR inhibitors against melanoma and non-melanoma skin cancers
Roy, Tithi,Boateng, Samuel T.,Banang-Mbeumi, Sergette,Singh, Pankaj K.,Basnet, Pratik,Chamcheu, Roxane-Cherille N.,Ladu, Federico,Chauvin, Isabel,Spiegelman, Vladimir S.,Hill, Ronald A.,Kousoulas, Konstantin G.,Nagalo, Bolni Marius,Walker, Anthony L.,Fotie, Jean,Murru, Siva,Sechi, Mario,Chamcheu, Jean Christopher
supporting information, (2021/01/14)
Due to hurdles, including resistance, ad...
Simultaneous Two-Color Visualization of Lipid Droplets and Endoplasmic Reticulum and Their Interplay by Single Fluorescent Probes in Lambda Mode
Guo, Lifang,Tian, Minggang,Zhang, Zhiyun,Lu, Qing,Liu, Zhiqiang,Niu, Guangle,Yu, Xiaoqiang
supporting information, p. 3169 - 3179 (2021/03/01)
In living systems, subcellular organelle...
577-85-5 Process route
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-
118-93-4,104809-67-8
o-hydroxyacetophenone
-
-
100-52-7
benzaldehyde
-
-
577-85-5,66585-05-5
3-hydroxyflavone
| Conditions | Yield |
|---|---|
|
With
pyrrolidine; oxygen;
In
water;
at 50 ℃;
under 760.051 Torr;
|
78%
|
|
o-hydroxyacetophenone; benzaldehyde;
With
methanol; sodium hydroxide;
for 3h;
Reflux;
With
dihydrogen peroxide;
at 20 ℃;
|
75%
|
|
o-hydroxyacetophenone; benzaldehyde;
With
sodium hydroxide;
In
ethanol; water;
for 12h;
With
dihydrogen peroxide;
In
ethanol; water;
for 12h;
|
70%
|
|
o-hydroxyacetophenone; benzaldehyde;
With
sodium hydroxide;
In
methanol;
at 20 ℃;
for 3h;
Reflux;
With
dihydrogen peroxide;
In
methanol; water;
at 20 ℃;
for 2h;
|
27%
|
|
Multi-step reaction
with
2
steps
1: sodium hydroxide / ethanol / 18 h / 20 °C
2: sodium hydroxide; dihydrogen peroxide / ethanol / 18 h / 4 - 20 °C
With
dihydrogen peroxide; sodium hydroxide;
In
ethanol;
|
|
|
Multi-step reaction
with
2
steps
1: sodium hydroxide / water; ethanol / 20 °C
2: sodium hydroxide; dihydrogen peroxide / water; methanol / 20 °C
With
dihydrogen peroxide; sodium hydroxide;
In
methanol; ethanol; water;
1: |Aldol Condensation;
|
|
|
Multi-step reaction
with
2
steps
1: potassium hydroxide / methanol / 20 °C
2: dihydrogen peroxide; sodium hydroxide / methanol; water / 20 °C
With
dihydrogen peroxide; potassium hydroxide; sodium hydroxide;
In
methanol; water;
2: |Algar-Flynn-Olyamada Reaction;
|
|
|
Multi-step reaction
with
2
steps
1: sodium hydroxide / ethanol
2: potassium hydroxide; dihydrogen peroxide / ethanol; water / 3 h / 0 °C
With
dihydrogen peroxide; potassium hydroxide; sodium hydroxide;
In
ethanol; water;
2: |Algar-Flynn-Olyamada Reaction;
|
|
|
Multi-step reaction
with
2
steps
1.1: potassium hydroxide / ethanol / 0.33 h / 25 °C
1.2: 0.83 h
2.1: potassium hydroxide; dihydrogen peroxide / ethanol / 0.02 h / Microwave irradiation
With
dihydrogen peroxide; potassium hydroxide;
In
ethanol;
1.1: |Claisen-Schmidt Condensation / 1.2: |Claisen-Schmidt Condensation / 2.1: |Algar-Flynn-Olyamada Reaction;
|
|
|
Multi-step reaction
with
2
steps
1.1: sodium hydroxide / ethanol / 0.5 h / 35 °C
2.1: sodium carbonate / methanol; water / 0.5 h / 0 °C
2.2: 24 h / 0 - 27 °C
With
sodium carbonate; sodium hydroxide;
In
methanol; ethanol; water;
1.1: |Claisen-Schmidt Condensation / 1.2: |Claisen-Schmidt Condensation / 2.2: |Algar-Flynn-Olyamada Reaction;
|
|
|
Multi-step reaction
with
2
steps
1: piperidine / ethanol / 3 h / Reflux
2: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran; methanol; water / 10 h / 0 °C
With
piperidine; dihydrogen peroxide; lithium hydroxide;
In
tetrahydrofuran; methanol; ethanol; water;
|
|
|
o-hydroxyacetophenone;
With
sodium hydroxide;
In
methanol; water;
for 0.5h;
benzaldehyde;
In
methanol; water;
at 20 ℃;
With
dihydrogen peroxide;
In
water;
at 20 ℃;
for 1h;
|
|
|
Multi-step reaction
with
2
steps
1.1: sodium hydroxide / methanol; water / 0.5 h / 20 °C
1.2: 4 h / 20 °C
2.1: dihydrogen peroxide / methanol; water / 1 h
With
dihydrogen peroxide; sodium hydroxide;
In
methanol; water;
1.1: |Claisen Condensation / 1.2: |Claisen Condensation / 2.1: |Algar-Flynn-Olyamada Reaction;
|
|
|
o-hydroxyacetophenone; benzaldehyde;
With
sodium hydroxide;
In
methanol;
With
dihydrogen peroxide;
In
water;
With
hydrogenchloride;
In
water;
|
|
|
Multi-step reaction
with
2
steps
1: potassium hydroxide / ethanol / 0.33 h / Microwave irradiation; Heating
2: potassium hydroxide; dihydrogen peroxide / methanol / 0.17 h / 40 °C / Microwave irradiation
With
dihydrogen peroxide; potassium hydroxide;
In
methanol; ethanol;
1: |Claisen-Schmidt Condensation / 2: |Algar-Flynn-Olyamada Reaction;
|
-
-
1214-47-7
1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one
-
-
577-85-5,66585-05-5
3-hydroxyflavone
| Conditions | Yield |
|---|---|
|
With
dihydrogen peroxide; sodium hydroxide;
In
ethanol; water;
at 0 - 20 ℃;
for 24h;
|
89%
|
|
With
dihydrogen peroxide; sodium hydroxide;
In
methanol; water;
at 20 ℃;
|
74%
|
|
With
dihydrogen peroxide; sodium hydroxide;
In
ethanol; water;
at 20 ℃;
for 12h;
|
60%
|
|
With
hydrogenchloride; dihydrogen peroxide; potassium hydroxide;
In
methanol;
at 25 ℃;
for 4h;
|
|
|
With
water; dihydrogen peroxide; sodium hydroxide;
In
methanol;
at 20 ℃;
Cooling with ice;
|
|
|
With
dihydrogen peroxide; sodium hydroxide;
In
ethanol;
at 4 - 20 ℃;
for 18h;
|
2.63 g
|
|
With
dihydrogen peroxide; sodium hydroxide;
In
ethanol;
at 4 - 20 ℃;
for 18h;
|
2.63 g
|
|
1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one;
With
sodium hydroxide;
In
tetrahydrofuran; ethanol; water;
at 0 ℃;
for 1h;
With
dihydrogen peroxide;
In
tetrahydrofuran; ethanol; water;
at 0 - 20 ℃;
|
|
|
Multi-step reaction
with
3
steps
1: triethylamine
2: dihydrogen peroxide; sodium hydroxide / ethanol / 4 h / 5 °C
3: montmorillonite KSF clay / 0.03 h / 120 °C / Microwave irradiation
With
dihydrogen peroxide; triethylamine; sodium hydroxide;
In
ethanol;
|
|
|
With
dihydrogen peroxide; potassium hydroxide;
In
ethanol; water;
at 0 ℃;
for 3h;
|
|
|
With
dihydrogen peroxide;
Inert atmosphere;
|
|
|
With
dihydrogen peroxide;
In
ethanol;
|
|
|
With
dihydrogen peroxide; sodium hydroxide;
In
methanol;
for 1h;
|
|
|
With
dihydrogen peroxide;
In
ethanol; water;
for 8h;
Cooling with ice;
|
|
|
With
dihydrogen peroxide;
In
methanol; water;
for 1h;
|
|
|
With
dihydrogen peroxide; potassium hydroxide;
In
methanol;
at 40 ℃;
for 0.166667h;
Microwave irradiation;
|
|
|
1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one;
With
sodium hydroxide;
In
methanol; water;
for 0.166667h;
Cooling with ice;
With
dihydrogen peroxide;
In
methanol; water;
at 20 ℃;
|
1.49 g
|
|
With
dihydrogen peroxide; sodium hydroxide;
In
ethanol; water;
at 20 - 50 ℃;
for 5.25h;
|
1.11 g
|
577-85-5 Upstream products
-
56-23-5
tetrachloromethane
-
128-08-5
N-Bromosuccinimide
-
1621-55-2
rac-trans-3-hydroxy-2-phenyl-3,4-dihydro-2H-chromen-4-one
-
94-36-0
dibenzoyl peroxide
577-85-5 Downstream products
-
7245-02-5
3-methoxyflavone
-
1603-46-9
3-hydroxy-2,3-dimethoxyflavan-4-one
-
70460-61-6
2,3-Diethoxy-3-hydroxy-2-phenyl-chroman-4-one
-
124513-20-8
2-phenylchromon-3-yl (trimethylsilyl)acetate
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