6-Hydroxyflavanone

Base Information

• Chemical Name: 6-Hydroxyflavanone
• CAS No.: 4250-77-5
• Molecular Formula: C15H12 O3
• Molecular Weight: 240.258
• Hs Code.: 2932999099
• European Community (EC) Number: 624-472-8
• UNII: 1F174812MP
• DSSTox Substance ID: DTXSID1022429
• Nikkaji Number: J285.121K
• Wikidata: Q27116092
• Metabolomics Workbench ID: 54981
• ChEMBL ID: CHEMBL195033
• Mol file: 4250-77-5.mol

Synonyms:6-Hydroxyflavanone;4250-77-5;6-hydroxy-2-phenylchroman-4-one;6-hydroxy-2-phenyl-2,3-dihydro-4H-chromen-4-one;Flavanone, 6-hydroxy-;(+/-)-6-Hydroxyflavanone;6-hydroxy-2-phenyl-2,3-dihydrochromen-4-one;4H-1-Benzopyran-4-one, 2,3-dihydro-6-hydroxy-2-phenyl-;6-Hydroxy-Flavanone;UNII-1F174812MP;1F174812MP;CHEMBL195033;CHEBI:34471;6-hydroxy-2-phenyl-chroman-4-one;MFCD00017485;Maybridge3_000570;6-Hydroxyflavanone, 99%;bmse000985;D0O0ZC;Oprea1_761592;SCHEMBL126598;6-hydroxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one;DTXSID1022429;XYHWPQUEOOBIOW-UHFFFAOYSA-;HMS1432J20;BDBM50296861;NSC804064;AKOS015856201;CCG-233325;NSC-804064;IDI1_011957;AS-60586;PD182938;FT-0621166;H1027;A872871;Q27116092;F0001-1180;InChI=1/C15H12O3/c16-11-6-7-14-12(8-11)13(17)9-15(18-14)10-4-2-1-3-5-10/h1-8,15-16H,9H2

Chemical Property of 6-Hydroxyflavanone

Chemical Property:

• Appearance/Colour: Slightly yellow-cream powder
• Vapor Pressure: 3.05E-09mmHg at 25°C
• Melting Point: 220-222 °C (dec.)(lit.)
• Boiling Point: 464.3ºC at 760 mmHg
• PKA: 9.53±0.40(Predicted)
• Flash Point: 181.2ºC
• PSA: 46.53000
• Density: 1.288g/cm3
• LogP: 3.09870
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 240.078644241
• Heavy Atom Count: 18
• Complexity: 309

Purity/Quality:

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

6-Hydroxyflavanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(OC2=C(C1=O)C=C(C=C2)O)C3=CC=CC=C3
• Uses: 6-Hydroxyflavanone (6-HF) has been used for the enantiomeric separation of flavonoids using polysaccharide-based chiral stationary phases by nano-liquid chromatography (nano-LC). Racemic 6-HF may be used in the synthesis of 6-propionoxy-flavanone (6-PF). 6-HF may be employed as synthetic flavone to investigate the mechanism of tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) induced cytotoxic and apoptotic effects in HeLa cancer cells.

Technology Process of 6-Hydroxyflavanone

There total 20 articles about 6-Hydroxyflavanone 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: 95.8%

6-methoxymethoxyflavanone → 6-hydroxyflavanone (4250-77-5)

Guidance literature:

With hydrogenchloride; In methanol; at 20 - 50 ℃; for 1h;

DOI:10.1248/cpb.53.547

Reference yield: 84.0%

benzaldehyde (100-52-7) + 2,5-Dihydroxyacetophenone (490-78-8) → 6-hydroxyflavanone (4250-77-5)

Guidance literature:

2,5-Dihydroxyacetophenone; With lithium hydroxide monohydrate; In methanol; at 5 ℃; for 0.166667h;

benzaldehyde; In methanol; at 20 ℃; for 144h;

DOI:10.1007/s10973-016-5896-6

Reference yield: 79.0%

6-hydroxy-2,3-dihydro-4H-chromen-4-one (80096-64-6) + phenylboronic acid (98-80-6) → 6-hydroxyflavanone (4250-77-5)

Guidance literature:

6-hydroxy-2,3-dihydro-4H-chromen-4-one; With [2,2]bipyridinyl; palladium(II) trifluoroacetate; oxygen; In 1,4-dioxane; dimethyl sulfoxide; at 100 ℃;

phenylboronic acid; With oxygen; trifluoroacetic acid; In 1,4-dioxane; dimethyl sulfoxide; at 80 ℃;

DOI:10.1021/acs.joc.9b01162

upstream raw materials:

benzaldehyde

2,5-Dihydroxyacetophenone

2’-hydroxy-5’-(methoxymethoxy)acetophenone

6-hydroxyflavone

Downstream raw materials:

3,6-dihydroxyflavone

6-hydroxy-3-benzylideneflavanone

3-benzylidene-2-phenyl-6-hydroxy-2,3-dihydro-4H-1-benzopyran-4-one

4-oxo-2-phenylchroman-6-yl acetate

Refernces

• 1、 He, Feng,Li, Na,Liu, Liyan,Luo, Huiqing,Wang, Huaqiao,Yang, Depo. "Flavanone-based fluorophores with aggregation-induced emission enhancement characteristics for mitochondria-imaging and zebrafish-imaging". . . Retrieved 2020/08/28.
• 2、 Cui, Wei,Zhang, Ji,Wang, Qian,Gao, Kai,Zhang, Wei,Yang, Jian. "A novel synthesis of naringenin and related flavanones". . p. 686 - 689. Retrieved 2015/02/19.