WEDELOLACTONE

Iupac Name：1,8,9-trihydroxy-3-methoxy-[1]benzofuro[3,2-c]chromen-6-one

Molecular Weight：314.2464

Modify Date.: 2022-11-05 08:55

Introduction: Wedelolactone, a natural product from Ecliptae herba, suppresses LPS-induced caspase-11 expression by directly inhibiting the IKK Complex[1]. Wedelolactone inhibits 5-lipoxygenase (5-Lox) (IC50~2.5 μM) activity by an oxygen radical scavenging mechanism. Wedelolactone induces caspase-dependent apoptosis in prostate cancer cells via downregulation of PKCε without inhibiting Akt[2]. Anti-cancer, anti-inflammatory, and antioxidant activities[3]. View more+

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1. Names and Identifiers

1.1 Name: WEDELOLACTONE
1.2 Synonyms: 1,8,9-Trihydroxy-3-methoxy-[1]benzofuro[3,2-c]chromen-6-one 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c][1]benzopyran-6-one 1,8,9-trihydroxy-3-Methoxy-6H-benzofuro[3,2-c]chroMen-6-one 5,11,12-Trihydroxy-7-MethoxycouMestan 6H-Benzofuro(3,2-C)(1)benzopyran-6-one, 1,8,9-trihydroxy-3-methoxy- 6H-Benzofuro[3,2-c][1]benzopyran-6-one, 1,8,9-trihydroxy-3-methoxy- 7-Methoxy-5,11,12-trihydroxycoumestan IKK Inhibitor II, Wedelolactone IKK Inhibitor II, Wedelolactone - CAS 524-12-9 - Calbiochem Wedelolactone

1.3 CAS No.: 524-12-9

1.4 CID: 5281813

1.5 Molecular Formula: C16H10O7 (isomer)

1.6 Inchi: InChI=1S/C16H10O7/c1-21-6-2-10(19)14-12(3-6)23-16(20)13-7-4-8(17)9(18)5-11(7)22-15(13)14/h2-5,17-19H,1H3

1.7 InChkey: XQDCKJKKMFWXGB-UHFFFAOYSA-N

1.8 Canonical Smiles: COC1=CC(=C2C(=C1)OC(=O)C3=C2OC4=CC(=C(C=C43)O)O)O

1.9 Isomers Smiles: COC1=CC(=C2C(=C1)OC(=O)C3=C2OC4=CC(=C(C=C43)O)O)O

2. Properties

2.1 Density: 1.655 g/cm³

2.1 Melting point: 315°C(lit.)

2.1 Boiling point: 498.4 oC at 760 mmHg

2.1 Refractive index: 1.758

2.1 Flash Point: 255.2 oC

2.1 Precise Quality: 314.04300

2.1 PSA: 113.27000

2.1 logP: 2.81780

2.1 Solubility: DMSO: 14?mg/mL, soluble

2.2 Λmax: 350(MeOH)nm

2.3 Appearance: solid

2.4 Storage: 2-8°C

2.5 Color/Form: Yellow powder

2.6 pKa: 6.90±0.20(Predicted)

2.7 Water Solubility: DMSO: 14?mg/mL, soluble

2.8 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A member of the class of coumestans that is coumestan with hydroxy substituents as positions 1, 8 and 9 and a methoxy substituent at position 3. WEDELOLACTONESupplier

4. Safety and Handling

4.1 Hazard Codes: Xn

4.1 Risk Statements: R22;R43

4.1 Safety Statements: 36/37

4.1 WGK Germany: 3

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin sensitization, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H317 May cause an allergic skin reaction
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

524-12-9Total: 17 Synthesis Route

108-73-6 210 Suppliers

524-12-9 63 Suppliers

Literatures:
Pandey, G.; Muralikrishna, C.; Bhalerao, U. T. Tetrahedron, 1989 , vol. 45, p. 6867 - 6874
Yield: null

139-85-5 371 Suppliers

524-12-9 63 Suppliers

Literatures:
Li, Chuang Chuang; Xie, Zhi Xiang; Zhang, Yan Dong; Chen, Jia Hua; Yang, Zhen Journal of Organic Chemistry, 2003 , vol. 68, # 22 p. 8500 - 8504
Yield: null

5447-02-9 72 Suppliers

524-12-9 63 Suppliers

Literatures:
Li, Chuang Chuang; Xie, Zhi Xiang; Zhang, Yan Dong; Chen, Jia Hua; Yang, Zhen Journal of Organic Chemistry, 2003 , vol. 68, # 22 p. 8500 - 8504
Yield: null

View all

7. Precursor and Product

precursor:

627489-15-0

627489-10-5

162888-73-5

139-85-5

627489-61-6

120-80-9

67964-24-3

27688-86-4

5447-02-9

1023744-97-9

344303-12-4

27688-85-3

17575-26-7

344303-15-7

627489-05-8

115623-32-0

108-73-6

91360-58-6

View all

8. Computational chemical data

Molecular Weight: 314.2464g/mol
Molecular Formula: C₁₆H₁₀O₇
Compound Is Canonicalized: True
XLogP3-AA: 2.4
Exact Mass: 314.04265265
Monoisotopic Mass: 314.04265265
Complexity: 483
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 7
Topological Polar Surface Area: 109
Heavy Atom Count: 23
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: AAADccB4OAAAAAAAAAAAAAAAAAAAASAAAAA0YIAAAAAAAEiR9AAAGgAACAAADASAmAIyDsAABkCIAqDSCAACCAAkIAAAiAEGiMgNJzaONRqCe2Gl4BUJuYfL7PzOoQABCAAIQABCAAIQABCAAAAAAAAAAA==

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