Jaceosidin

Iupac Name：5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxychromen-4-one

Molecular Weight：330.28886

Modify Date.: 2022-11-22 20:49

Introduction:

Jaceosidin is a flavonoid isolated from Artemisia vestita, induces apoptosis in cancer cells, activates Bax and down-regulates Mcl-1 and c-FLIP expression[1]. Jaceosidin exhibits anti-cancer[2], anti-inflammatory activities, decreases leves of inflammatory markers, and suppresses COX-2 expression and NF-κB activation[3].

Jaceosidin is a trihydroxyflavone that is flavone with hydroxy groups at positions 5, 7 and 4' and methoxy groups at positions 3' and 6. Isolated from Salvia tomentosa and Artemisia asiatica, it exhibits anti-allergic, anti-inflammatory and apoptosis inducing activties. It has a role as a metabolite, an anti-inflammatory agent, an apoptosis inducer, an anti-allergic agent and an antineoplastic agent. It is a trihydroxyflavone and a dimethoxyflavone.

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1. Names and Identifiers

1.1 Name: Jaceosidin
1.2 Synonyms: 3',6-Dimethoxy-4',5,7-trihydroxyflavone 3′,6-Dimethoxy-4′,5,7-trihydroxyflavone 4',5,7-Trihydroxy-3',6-dimethoxyflavone 4′,5,7-Trihydroxy-3′,6-dimethoxyflavone 4′-Demethyleupatilin 4'-Demethyleupatilin 4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxy- 5,7,4′-Trihydroxy-6,3′-dimethoxyflavone 5,7,4'-trihydroxy-3',6-dimethoxyflavone 5,7,4'-Trihydroxy-6,3'-dimethoxyflavone 5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxy-4H-1-benzopyran-4-one 5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxy-4H-chromen-4-one 5,7-dihydroxy-2-(4-hydroxy-3-methoxy-phenyl)-6-methoxy-chromen-4-one 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxychromen-4-one 6-Hydroxyluteolin 3',6-dimethyl ether 6-Hydroxyluteolin 6,3′-dimethyl ether 6-Hydroxyluteolin 6,3'-dimethyl ether 6-Methoxyluteolin 3′-methyl ether 6-Methoxyluteolin 3'-methyl ether 6-methoxyluteolin-3'-methyl ether Flavone, 4′,5,7-trihydroxy-3′,6-dimethoxy- Flavone,4',5,7-trihydroxy-3',6-dimethoxy- (7CI,8CI) Jaceosidin JACEOSIDINE Jacesiolin Jaseocidin

1.3 CAS No.: 18085-97-7

1.4 CID: 5379096

1.5 Molecular Formula: C17H14O7 (isomer)

1.6 Inchi: InChI=1S/C17H14O7/c1-22-13-5-8(3-4-9(13)18)12-6-10(19)15-14(24-12)7-11(20)17(23-2)16(15)21/h3-7,18,20-21H,1-2H3

1.7 InChkey: GLAAQZFBFGEBPS-UHFFFAOYSA-N

1.8 Canonical Smiles: COC1=C(C=CC(=C1)C2=CC(=O)C3=C(O2)C=C(C(=C3O)OC)O)O

1.9 Isomers Smiles: COC1=C(C=CC(=C1)C2=CC(=O)C3=C(O2)C=C(C(=C3O)OC)O)O

2. Properties

2.1 Density: 1.483

2.1 Melting point: 259-260 °C

2.1 Boiling point: 619°Cat760mmHg

2.1 Refractive index: 1.67

2.1 Flash Point: 232°C

2.1 Precise Quality: 330.07400

2.1 PSA: 109.36000

2.1 logP: 2.59400

2.1 Color/Form: Yellow powder

2.2 pKa: 6.47±0.40(Predicted)

3. Use and Manufacturing

3.1 Definition: ChEBI: A trihydroxyflavone that is flavone with hydroxy groups at positions 5, 7 and 4' and methoxy groups at positions 3' and 6. Isolated from Salvia tomentosa and Artemisia asiatica, it exhibits anti-allergic, anti-inflammatory and apotosis inducing activties. JaceosidinSupplier

4. Safety and Handling

4.1 Specification: 4',5,7-Trihydroxy-3',6-dimethoxyflavone (CAS No.18085-97-7), its synonyms are 4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxy- ; 5,7-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6-methoxy-4H-chromen-4-one ; 5,7-Dihydroxy-2-(4-hydroxy-3-methoxy-phenyl)-6-methoxy-chromen-4-one ; 6-Methoxyluteolin-3'-methyl ether .

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s)	no data available
Signal word	no data available
Hazard statement(s)	no data available
Precautionary statement(s)
Prevention	no data available
Response	no data available
Storage	no data available
Disposal	no data available

2.3 Other hazards which do not result in classification

no data available

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6. Synthesis Route

18085-97-7Total: 4 Synthesis Route

121-33-5 637 Suppliers

18085-97-7 56 Suppliers

Literatures:
Bioorganic and Medicinal Chemistry Letters, , vol. 22, # 7 p. 2534 - 2535
Yield: null

51145-80-3

18085-97-7 56 Suppliers

Literatures:
Bioorganic and Medicinal Chemistry Letters, , vol. 22, # 7 p. 2534 - 2535
Yield: null

22248-14-2 5 Suppliers

18085-97-7 56 Suppliers

Literatures:
Bioorganic and Medicinal Chemistry Letters, , vol. 22, # 7 p. 2534 - 2535
Yield: null

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7. Precursor and Product

precursor:

51145-80-3

121-33-5

137527-38-9

22248-14-2

8. Other Information

8.0 Metabolism: Jaceosidine is a known human metabolite of eupatilin.

8.1 Mesh Entry Terms: jaceosidin

8.2 Use Classification: Polyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]

8.3 Definition: ChEBI: A trihydroxyflavone that is flavone with hydroxy groups at positions 5, 7 and 4' and methoxy groups at positions 3' and 6. Isolated from Salvia tomentosa and Artemisia asiatica, it exhibits anti-allergic, anti-inflammatory and apo tosis inducing activties.

9. Computational chemical data

Molecular Weight: 330.28886g/mol
Molecular Formula: C₁₇H₁₄O₇
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 330.07395278
Monoisotopic Mass: 330.07395278
Complexity: 505
Rotatable Bond Count: 3
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 7
Topological Polar Surface Area: 105
Heavy Atom Count: 24
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccB4OAAAAAAAAAAAAAAAAAAAAAAAAAAwYIAAAAAAAACBQAAAGgAACAAADASAmAIyBoAABgCIAqBSAAACCAAkIAAIiAEGiMgNJzaGNRqCeWOl4BULuQfK7LzOIQABCAAIQABCAAIQABCAAAAAAAAAAA==

10. Question & Answer

Biological Activity of Jaceosidin Mar 31 2021
Jaceosidin, also known as 4',5,7-trihydroxy-3',6-dimethoxyflavone, is a member of the class of compounds known as 6-o-methylated flavonoids. 6-o-methylated flavonoids are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. Thus, jaceosidin is considered to be a...

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