CAS Number6199-67-3
Synonyms19-Nor-9β,10α-lanosta-5,23-diene-3,11,22-trione, 2β,16α,20,25-tetrahydroxy-9-methyl-, 25-acetate; 1,2-Dihydro-a-elaterin; Cucurbitacin B hydrate; 19-nor-9β,10α-Lanosta-5,23-diene-3,11,22-trione, 9-methyl-2β,16α,20,25-tetrahydroxy-, 25-acetate; 1,2-Dihydro-α-elaterin; 25-(Acetyloxy)-2b,16a,20-trihydroxy-9b-methyl-19-nor-10a-lanosta-5,23E-diene-3,11,22-trione
Molecular FormulaC32H46O8
Molecular Weight558.70 (anhydrous basis)
Purity≥97 (HPLC)%
Density1.2±0.1 g/cm3
Boiling Point699.3±55.0 °C at 760 mmHg
Melting Point184-186ºC
Appearancepowder
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 6199-67-3 |
| Catalog No. | 2A-9032577 |
| Chinese Name | 葫芦素B |
| Synonyms | 19-Nor-9β,10α-lanosta-5,23-diene-3,11,22-trione, 2β,16α,20,25-tetrahydroxy-9-methyl-, 25-acetate; 1,2-Dihydro-a-elaterin; Cucurbitacin B hydrate; 19-nor-9β,10α-Lanosta-5,23-diene-3,11,22-trione, 9-methyl-2β,16α,20,25-tetrahydroxy-, 25-acetate; 1,2-Dihydro-α-elaterin; 25-(Acetyloxy)-2b,16a,20-trihydroxy-9b-methyl-19-nor-10a-lanosta-5,23E-diene-3,11,22-trione |
| Molecular Formula | C32H46O8 |
| Molecular Weight | 558.70 (anhydrous basis) |
| Purity | ≥97 (HPLC) |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 699.3±55.0 °C at 760 mmHg |
| Melting Point | 184-186ºC |
| Appearance | powder |
| Storage Condition | The warehouse is low-temperature, ventilated, dry, |
| Packaging | II |
| Application | Cucurbitacin B is a natural compound with anti-cancer activity. |
| PubChem ID | 329775173 |
| MDL Number | MFCD07778083 |
| 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 |
| InChI | 1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12+/t19-,20+,21-,22+,25+,29+,30-,31+,32+/m1/s1 |
| InChI Key | IXQKXEUSCPEQRD-DKRGWESNSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | transportation |
| MSDS | msds/32577_1_6199_67_3.pdf |
| Bioactivity | Cucurbitacin B belongs to a class of highly oxidized tetracyclic triterpenoids; could repress cancer cell progression.IC50 value:Target: anticancer natural compoundin vitro: Cucurbitacin-B inhibited growth and modulated expression of cell-cycle regulators in SHSY5Y cells. At the molecular level, we found that Cucurbitacin-B inhibited AKT signaling activation through up-regulation of PTEN [1]. CuB induced apoptosis of A549 cells in a -concentration-dependent manner, as determined by fluorescence microscopy, flow cytometry and transmission electron microscopy. CuB dose-dependently inhibited lung cancer cell proliferation, with cell cycle inhibition and cyclin B1 downregulation. Apoptosis induced by CuB was shown to be associated with cytochrome c release, B-cell lymphoma 2 downregulation and signal transducer and activator of transcription 3 pathway inhibition [2]. CuB inhibited ITGA6 and ITGB4 (integrin α6 and integrin β4), which are overexpressed in breast cancer. Furthermore, CuB also induced the expression of major ITGB1and ITGB3, which are known to cause integrin-mediated cell death [3]. Cuc B treatment caused DNA double-strand breaks (DSBs) without affecting the signal transducer and activator of transcription 3 (STAT3), the potential molecular target for Cuc B. Cuc B triggers ATM-activated Chk1-Cdc25C-Cdk1, which could be reversed by both ATM siRNA and Chk1 siRNA. Cuc B also triggers ATM-activated p53-14-3-3-σ pathways, which could be reversed by ATM siRNA [4].in vivo: Efficacy of CuB was tested in vivo using two different orthotopic models of breast cancer. MDA-MB-231 and 4T-1 cells were injected orthotopically in the mammary fat pad of female athymic nude mice or BALB/c mice respectively. Our results showed that CuB administration inhibited MDA-MB-231 orthotopic tumors by 55%, and 4T-1 tumors by 40%. The 4T-1 cells represent stage IV breast cancer and form very aggressive tumors [3]. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Cytoskeleton >> Integrin Research Areas >> Cancer Natural Products >> Terpenoids and Glycosides References [1]. Shang Y, et al. Cucurbitacin-B inhibits neuroblastoma cell proliferation through up-regulation of PTEN. Eur Rev Med Pharmacol Sci. 2014;18(21):3297-303. [2]. Zhang M, et al. Cucurbitacin B inhibits proliferation and induces apoptosis via STAT3 pathway inhibition in A549 lung cancer cells. Mol Med Rep. 2014 Dec;10(6):2905-11. [3]. Gupta P, et al. Inhibition of Integrin-HER2 signaling by Cucurbitacin B leads to in vitro and in vivo breast tumor growth suppression. Oncotarget. 2014 Apr 15;5(7):1812-28. [4]. Guo J, et al. Cucurbitacin B induced ATM-mediated DNA damage causes G2/M cell cycle arrest in a ROS-dependent manner. PLoS One. 2014 Feb 4;9(2):e88140. Chemical & Physical Properties Density 1.2±0.1 g/cm3 Boiling Point 699.3±55.0 °C at 760 mmHg Melting Point 184-186ºC Molecular Formula C32H46O8 Molecular Weight 558.703 Flash Point 218.8±25.0 °C Exact Mass 558.319275 PSA 138.20000 LogP 2.31 Vapour Pressure 0.0±5.0 mmHg at 25°C Index of Refraction 1.568 InChIKey IXQKXEUSCPEQRD-DKRGWESNSA-N SMILES CC(=O)OC(C)(C)C=CC(=O)C(C)(O)C1C(O)CC2(C)C3CC=C4C(CC(O)C(=O)C4(C)C)C3(C)C(=O)CC12C |
| Use of | Properties Name cucurbitacin B Synonym More Synonyms Cucurbitacin B Biological Activity Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Cytoskeleton >> Integrin Research Areas >> Cancer Natural Products >> Terpenoids and Glycosides References [1]. Shang Y, et al. Cucurbitacin-B inhibits neuroblastoma cell proliferation through up-regulation of PTEN. Eur Rev Med Pharmacol Sci. 2014;18(21):3297-303. [3]. Gupta P, et al. Inhibition of Integrin-HER2 signaling by Cucurbitacin B leads to in vitro and in vivo breast tumor growth suppression. Oncotarget. 2014 Apr 15;5(7):1812-28. Chemical & Physical Properties Molecular Formula C32H46O8 Exact Mass 558.319275 PSA 138.20000 Index of Refraction 1.568 InChIKey IXQKXEUSCPEQRD-DKRGWESNSA-N |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Dangerous Regulations for land transport: 2811 International Dangerous Regulations for sea transport: 2811 International Dangerous Regulations for air transport: 2811 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: TOXIC SOLID, ORGANIC, N.O.S. (Cucurbitacin B hydrate) IMDG Code: TOXIC SOLID, ORGANIC, N.O.S. (Cucurbitacin B hydrate) International air transport hazard regulations: Toxic solid, organic, n.o.s. (Cucurbitacin B hydrate) 14.3 Transport hazard categories European Land Transport Danger Regulations: 6.1 International Maritime Transport Danger Regulations: 6.1 International Air Transport Danger Regulations: 6.1 14.4 Package group European Dangerous Regulations for land transport: I International Dangerous Regulations for sea transport: I International Dangerous Regulations for air transport: I 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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