WITHAFERIN A

Molecular Weight：470.606

Modify Date.: 2022-11-29 02:21

Introduction: Withaferin A is a promising anticancer constituent of Ayurvedic medicinal plant Withania somnifera. Withaferin A showed potent cytotoxicity against human head and neck squamous cell carcinoma (JMAR and MDA-1986). View more+

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1. Names and Identifiers

1.1 Name: WITHAFERIN A
1.2 Synonyms: 5,6-beta-epoxy-4-beta,22,27-trihydroxy-1-5-beta-ergosta-24-dien-26-oicacid 5,6-Epoxy-5H-cyclopenta[a]phenanthrene, ergosta-2,24-dien-26-oic acid deriv. 5β-Ergosta-2,24-dien-26-oic acid, 5,6β-epoxy-4β,22,27-trihydroxy-1-oxo-, δ-lactone, (20S,22R)- delta-lactone,(20s,22r)-oxo Ergosta-2,24-dien-26-oic acid, 5,6-epoxy-4,22,27-trihydroxy-1-oxo-, δ-lactone, (4β,5β,6β,22R)- NSC 101088 NSC 273757 nsc-101088 WITHAFERIN A Withaferine Withaferine A

1.3 CAS No.: 5119-48-2

1.4 CID: 265237

1.5 Molecular Formula: C28H38O6 (isomer)

1.6 Inchi: InChI=1S/C28H38O6/c1-14-11-21(33-25(32)17(14)13-29)15(2)18-5-6-19-16-12-24-28(34-24)23(31)8-7-22(30)27(28,4)20(16)9-10-26(18,19)3/h7-8,15-16,18-21,23-24,29,31H,5-6,9-13H2,1-4H3/t15-,16-,18+,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1

1.7 InChkey: DBRXOUCRJQVYJQ-CKNDUULBSA-N

1.8 Canonical Smiles: CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3CC5C6(C4(C(=O)C=CC6O)C)O5)C)CO

1.9 Isomers Smiles: CC1=C(C(=O)O[C@H](C1)[C@@H](C)[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3C[C@@H]5[C@]6([C@@]4(C(=O)C=C[C@@H]6O)C)O5)C)CO

2. Properties

2.1 Density: 1.28

2.1 Melting point: 252-253℃

2.1 Boiling point: 680.7°C at 760 mmHg

2.1 Refractive index: 1.599

2.1 Flash Point: 226.7°C

2.1 Precise Quality: 470.26700

2.1 PSA: 96.36000

2.1 logP: 3.35290

2.1 Chemical Properties: Solid

2.2 Color/Form: Powder

2.3 pKa: 13.49±0.70(Predicted)

2.4 StorageTemp: Desiccate at -20°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 27 (the 4beta,5beta,6beta,22R stereoisomer). Isolated from Physlis longifolia, it exhibits cytotoxic activity.

3.2 Usage: Withaferin A is a promising anticancer constituent of Ayurvedic medicinal plant Withania somnifera. Withaferin A showed potent cytotoxicity against human head and neck squamous cell carcinoma (JMAR and MDA-1986).

4. Safety and Handling

4.1 Hazard Codes: T

4.1 Safety Statements: A poison by intraperitoneal route. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.

4.1 RIDADR: NONH for all modes of transport

4.1 WGK Germany: 3

4.1 RTECS: KE7288500

4.1 Safety: A poison by intraperitoneal route. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.
Hazard Codes:T

4.2 Specification: Withaferin A , its cas register number is 5119-48-2. It also can be called 5-19-06-00604 (Beilstein Handbook Reference) ; BRN 1335150 ; NSC 273757 ; NSC-101088 ; WITHAFERIN DERIV JPR, IOWA U. COMPOUND ; Withaferine A ; (4beta,5beta,6beta,22R)-5,6-Epoxy-4,22,27-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid, delta-lactone ; 5-beta-Ergosta-2,24-dien-26-oic acid, 5,6-beta-epoxy-4-beta,22,27-trihydroxy-1-oxo-, delta-lactone, (20S,22R)- ; 5beta-Ergosta-2,24-dien-26-oic acid, 5,6beta-epoxy-4beta,22,27-trihydroxy-1-oxo-, delta-lactone, (20S,22R)-(8CI) ; Ergosta-2,24-dien-26-oic acid, 5,6-epoxy-4,22,27-trihydroxy-1-oxo-, gamma-lactone, (4bta,5beta,6beta,22R)- . Withaferin A (CAS NO.5119-48-2) is should be isolated from leaves of Withania somnifera Dun.

4.3 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	54mg/kg (54mg/kg)		Toxicon. Vol. 8, Pg. 154, 1970.

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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. NMR Spectrum

Predict 1H proton NMR

7. Synthesis Route

5119-48-2Total: 7 Synthesis Route

674-26-0 49 Suppliers

5788-94-3

5119-48-2 15 Suppliers

Literatures:
Veleiro, Adriana S.; Burton, Gerardo; Gros, Eduardo G. Phytochemistry (Elsevier), 1985 , vol. 24, # 10 p. 2263 - 2266
Yield: null

81345-21-3

5119-48-2 15 Suppliers

Literatures:
Hirayama; Gamoh; Ikekawa Tetrahedron Letters, 1982 , vol. 23, # 45 p. 4725 - 4728
Yield: null

81874-42-2

5119-48-2 15 Suppliers

Literatures:
Hirayama; Gamoh; Ikekawa Tetrahedron Letters, 1982 , vol. 23, # 45 p. 4725 - 4728
Yield: null

View all

8. Precursor and Product

precursor:

674-26-0

85427-87-8

81874-42-2

81426-86-0

81345-21-3

81426-84-8

81426-85-9

product :

1214886-35-7

22848-79-9

9. Other Information

9.0 Livertox Summary: Ashwagandha is a popular Ayurvedic herb used as a general tonic, to increase energy and reduce stress. Ashwagandha has not been implicated in causing serum enzyme elevations during therapy, but recently has been implicated in rare cases of clinically apparent liver injury.

9.1 Drug Classes: Herbal and Dietary Supplements

9.2 Mesh Entry Terms: 5,6-epoxy-4,22,27-trihydroxy-1-oxoergosta-2,24-dienoic acid delta-lactone

10. Computational chemical data

Molecular Weight: 470.606g/mol
Molecular Formula: C₂₈H₃₈O₆
Compound Is Canonicalized: True
XLogP3-AA: 3.8
Exact Mass: 470.26683893
Monoisotopic Mass: 470.26683893
Complexity: 999
Rotatable Bond Count: 3
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 6
Topological Polar Surface Area: 96.4
Heavy Atom Count: 34
Defined Atom Stereocenter Count: 11
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: AAADcfB4OAAAAAAAAAAAAAAAEgAAAYAAAAAwYIEABIAAAGDAAAAAGgAACAAAD1SggAICCAAABgCIAqDSCAAAAAAgAAAICAEAAEgBFBYAIQACUAAF4AALMYOKyPCPgAAAAAAAAADAAAYAADAAAQAACAAAAA==

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12. Realated Product Infomation

1214886-35-7 27-O-acetyl-withaferin A

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