Cucurbitacin B

Description

Cucurbitacin B · CAS 6199-67-3 · C32H46O8. UNII 0115W5MABF. Melting Point: 184-186 °C.

Identification

CAS Registry Number	6199-67-3
PubChem CID	5281316
Molecular formula	C32H46O8
IUPAC name	[(E,6R)-6-[(2S,8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate
UNII (FDA)	0115W5MABF

Computed Descriptors

Molecular Weight	558.7
XLogP3	2.6
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	6
Exact Mass	558.31926842
Monoisotopic Mass	558.31926842
Topological Polar Surface Area	138
Heavy Atom Count	40
Formal Charge	0

Physical & Chemical Properties

Melting Point	184-186 °C

Physical description & handling notes

• Solid; [Merck Index]
• CRYSTALS FROM ABSOLUTE ETHANOL
• SPECIFIC OPTICAL ROTATION: +88 DEG @ 25 °C/D (ETHANOL, 1.55%)

GHS Hazard Classification

Reported hazard statements	H300 (100%)

Documented Uses

• Cucurbitacins: Isolated from cucurbitaceous plants and used as vermifuges, emetics, narcotics, and antimalarials; Reported cause of livestock poisoning in South Africa; [Merck Index] Highly toxic substance in wild cucumbers; [HSDB]
• ENSLIN, J SCI FOOD AGR 5, 410 (1954); ENSLIN ET AL, J SCI FOOD 8, 673 (1957); EISENHUT, NOLLER, J ORG CHEM 23, 1984 (1958); LAVIE, WILLNER, J AM CHEM SOC 80, 710 (1958). STRUCTURE: LAVIE ET AL, CHEM & IND (LONDON) 1959, 951; DE KOCK ET AL, J CHEM SOC 1963, 3828; VAN DER MERWE ET AL, J CHEM SOC 1963, 4275. STEREOCHEMISTRY: LAVIE ET AL, J ORG CHEM 28, 1790 (1963). /CUCURBITACINS B, D, & F/
• EIGHT BIOLOGICALLY ACTIVE CUCURBITACINS ISOLATED FROM ROOTS OF BRYONIA ALBA, INCLUDING CUCURBITACIN B, WERE CYTOTOXIC IN TISSUE CULTURES OF KB & HELA CELLS. CUCURBITACIN B WAS EFFECTIVE ON TRANSPLANTABLE SARCOMA 180 & EHRLICH ASCITES CARCINOMA IN MICE.
• IN RATS WITH IM WALKER CARCINOSARCOMA 256 & IN MICE WITH LEWIS LUNG CARCINOMA, ADMIN OF CUCURBITACIN B 0.8-1.6 MG/KG INHIBITED TUMOR DEVELOPMENT BUT THE LOW MARGIN BETWEEN ACTIVE & TOXIC DOSES RENDERED THE MATERIAL UNPROMISING AS A THERAPEUTIC AGENT.

Synonyms

Cucurbitacin B; 6199-67-3; Amarine; Datisca principle B; Cucurbitacine B; (+)-Cucurbitacin B; Datiscn Principle B; 1,2-Dihydro-alpha-elaterin; NSC-49451; NSC-144154; 0115W5MABF; CHEBI:3941; DTXSID501316196; 25-(Acetyloxy)-2,16,20-trihydroxy-9-methyl-19-norlanosta-5,23-diene-3,11,22-trione; RefChem:128713; DTXCID401746059

Frequently Asked Questions

What are the CAS number and molecular formula of Cucurbitacin B?

CAS 6199-67-3; molecular formula C32H46O8; molecular weight — g/mol.

What other names is Cucurbitacin B known by?

Cucurbitacin B, 6199-67-3, Amarine, Datisca principle B, Cucurbitacine B, (+)-Cucurbitacin B.

Is Cucurbitacin B classified as hazardous?

Hazard statements reported: H300.

What are the key physical properties of Cucurbitacin B?

Melting Point: 184-186 °C.

Facts on this page are taken from PubChem (US National Library of Medicine) and Wikidata. Grade-specific data — assay, moisture, particle size, packaging, shelf life — is issued per batch on the COA and is not published here.