ChemicalBook--->CAS DataBase List--->6199-67-3

6199-67-3

6199-67-3 Structure

6199-67-3 Structure
IdentificationBack Directory
[Name]

CUCURBITACIN B
[CAS]

6199-67-3
[Synonyms]

Cuc B
AMARINE
HSDB 3476
DATISCACIN
NSC-144154
heMsecin A
Cucurbitacin
cucurbitacineb
CUCURBITACIN B
BCucurbitacin B
CUCURBITACIN B(P)
CUCURBITACIN B(RG)
Cucurbitacin B ,97%
Cucurbitacin B, >99%
Cucurbitacin B hydrate
CUCURBITACIN B USP/EP/BP
1,2-DIHYDRO-ALPHA-ELATERIN
Dihydrocucurbitacin F-25-acetate
Cucurbitacin B, froM CucuMis Melo
Cucurbitacin B, 98%, from Cucumis melo
(2beta,9beta,10alpha,16alpha,23e)-thyl
Cucurbitacin B, 98%, from Cucumis melo L.
CAS?6199-67-3?Combretastatin A4 (Z) -Combretastatin A4 CAS 117048-59-6
(23E)-25-(Acetyloxy)-2β,16α,20-trihydroxycucurbita-5,23-diene-3,11,22-trione
19-nor-9-beta,10-alpha-lanosta-5,23-diene-3,11,22-trione,2-beta,16-alpha,20,25
19-nor-9beta,10alpha-lanosta-5,23-diene-3,11,22-trione,2beta,16alpha,20,25-tet
19-norlanosta-5,23-diene-3,11,22-trione,25-(acetyloxy)-2,16,20-trihydroxy-9-me
25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-19-norlanosta-5,23-diene-3,11,22-tr
(9β,10α,23E)-25-(Acetyloxy)-2β,16α,20-trihydroxy-9-methyl-19-norlanosta-5,23-diene-3,11,22-trione
(2β,9β,10α,16α,23E)-25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-19-Norlanosta-5,23-diene-3,11,22-trione
19-Norlanosta-5,23-diene-3,11,22-trione, 25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-, (2β,9β,10α,16α,23E)-
[Molecular Formula]

C32H46O8
[MDL Number]

MFCD07778083
[MOL File]

6199-67-3.mol
[Molecular Weight]

558.7
Chemical PropertiesBack Directory
[Melting point ]

184-186°
[alpha ]

D25 +88° (c = 1.55 in ethanol)
[Boiling point ]

546.74°C (rough estimate)
[density ]

1.0953 (rough estimate)
[refractive index ]

1.4900 (estimate)
[storage temp. ]

2-8°C
[solubility ]

DMSO: soluble10mg/mL, clear
[form ]

powder
[pka]

12.60±0.29(Predicted)
[color ]

white to beige
[λmax]

290nm(EtOH)(lit.)
[Merck ]

14,2614
[Stability:]

Hygroscopic
[Cosmetics Ingredients Functions]

SKIN CONDITIONING
[InChIKey]

IXQKXEUSCPEQRD-ALLWXVAWSA-N
[SMILES]

CC1(C)C([C@@H](O)C[C@]2([H])C1=CC[C@]([C@@](C[C@@H](O)[C@]3([H])[C@@](C)(O)C(/C=C/C(C)(C)OC(C)=O)=O)(C)[C@]3(C)C4)([H])[C@@]2(C)C4=O)=O
Safety DataBack Directory
[Hazard Codes ]

T
[Risk Statements ]

25
[Safety Statements ]

45-24/25
[RIDADR ]

UN 2811 6.1 / PGI
[WGK Germany ]

3
[RTECS ]

RC6190000
[HazardClass ]

6.1
[PackingGroup ]

II
[HS Code ]

29153900
[Storage Class]

6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials
[Hazard Classifications]

Acute Tox. 2 Oral
[Hazardous Substances Data]

6199-67-3(Hazardous Substances Data)
[Toxicity]

LD10 orally in mice: 5 mg/kg (LeMen)
Hazard InformationBack Directory
[Description]

Cucurbitacin B is a tetracyclic triterpenoid that has been shown to have a strong antitumor activity.
[Chemical Properties]

White solid
[Uses]

Cucurbitacin B hydrate has been used:
  • as a signal transducer and activator of transcription 3 (stat3) inhibitor to determine its effect on the expression of human lysosomal acid lipase (hLAL) in myeloid-derived suppressor cells (MDSCs).
  • as an ecdysone receptor (EcR) antagonist injection to lower the levels of 20-hydoxyecdysone (20E) signaling in butterflies.
  • to determine its effect on the cell viability of pancreatic cancer cell lines.

[Definition]

ChEBI: A cucurbitacin in which a lanostane skeleton is multi-substituted with hydroxy, methyl and oxo substituents, with unsaturation at positions 5 and 23; a hydroxy function at C-25 is acetylated.
[Biochem/physiol Actions]

Cucurbitacin B is a triterpenoid constituent of Cucurbitaceae plant species. Cucurbitacin B inhibits proliferation in a wide variety of tumor cell lines (IC50 15-30 nM) by inducing apoptosis and inducing cell cycle arrest at G2/M phase. Although the mechanism of action is unclear, Cucurbitacin B inhibits STAT 3 phosphorylation and expression levels and has been shown to block JAK2 activity. Curcubitacin B also inhibits the transcriptional activity of HIF1a and Nf-KB. Curcubitacin B is structurally similar to the JAK inhibitor Curcubitacin I.
Spectrum DetailBack Directory
[Spectrum Detail]

CUCURBITACIN B(6199-67-3)1HNMR
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