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zerumbone

Product Name
zerumbone
CAS No.
471-05-6
Chemical Name
zerumbone
Synonyms
zerumbone;Zerumbone-RM;ZeruMbone (6CI,7CI);Zingiber zerumbe extract;GIHNTRQPEMKFKO-SKTNYSRSSA-N;(2E,6E,10E)-2,6,9,9-Tetramethylcycloundeca-2,6,10-trienone;(2E,6E,10E)-2,6,9,9-tetramethylcycloundeca-2,6,10-trien-1-one;(2E,6E,10E)-2,6,9,9-Tetramethyl-2,6,10-cycloundecatrien-1-one;2,6,10-Cycloundecatrien-1-one, 2,6,9,9-tetramethyl-, (2E,6E,10E)-
CBNumber
CB41346756
Molecular Formula
C15H22O
Formula Weight
218.33
MOL File
471-05-6.mol
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zerumbone Property

Melting point:
67-69℃
Boiling point:
321.6±42.0 °C(Predicted)
Density 
0.887±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO: ≥10mg/mL
form 
powder
color 
white to off-white
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month.
LogP
4.168 (est)
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Safety

Hazard Codes 
Xi,N
Risk Statements 
43-50
Safety Statements 
36/37-60-61
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H317May cause an allergic skin reaction

H400Very toxic to aquatic life

Precautionary statements

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
Z3902
Product name
Zerumbone
Purity
≥98% (HPLC)
Packaging
10mg
Price
$84.1
Updated
2024/03/01
Sigma-Aldrich
Product number
Z3902
Product name
Zerumbone
Purity
≥98% (HPLC)
Packaging
50mg
Price
$171
Updated
2024/03/01
Cayman Chemical
Product number
15400
Product name
Zerumbone
Purity
≥99%
Packaging
5mg
Price
$38
Updated
2024/03/01
Cayman Chemical
Product number
15400
Product name
Zerumbone
Purity
≥99%
Packaging
10mg
Price
$61
Updated
2024/03/01
Cayman Chemical
Product number
15400
Product name
Zerumbone
Purity
≥99%
Packaging
50mg
Price
$234
Updated
2024/03/01
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zerumbone Chemical Properties,Usage,Production

Description

Zerumbone (471-05-6) is a natural sesquiterpene ketone isolated from Zingiber sp. Potentiates TRAIL-induced apoptosis via upregulation of death receptor DR4 and DR5 expression. Zerumbone induces apoptosis in T-acute lymphoblastic leukemia cells but has no cytotoxic effect on normal cells. Cell permeable.

Uses

Zerumbone has been used:

  • for liquid chromatography with mass spectrometry (LC-MS-MS)
  • to investigate its potential application in the prevention
  • treatment of esophageal squamous cell carcinomas (ESCC)

Definition

ChEBI: A sesquiterpenoid and cyclic ketone that is (1E,4E,8E)-alpha-humulene which is substituted by an oxo group at the carbon atom attached to two double bonds. It is obtained by steam distillati n from a type of edible ginger, Zingiber zerumbet Smith, grown particularly in southeast Asia.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biochem/physiol Actions

Zerumbone is a TRAIL-induced apoptosis potentiator. It potentiates TRAIL-induced apoptosis through the up-regulation of DR4 and DR5 expression and the down-regulation of cFLIP. Zerumbone has very little or no cytotoxic effect on the normal human endothelial cells and dermal fibroblasts. Zerumbone is a sesquiterpene isolated from in Zingiber zerumbet Smith (wild ginger).

Anticancer Research

Zerumbone is isolated from the rhizomes of the wild ginger Zingiber zerumbet. It isfound to suppress the proliferation of breast cancer and colon cancer cells and alsoto prevent initiation and promotion of skin cancer in mice. It also suppresses theNF-κB activation and its sequential suppression of IκBα kinase activity, IκBαphosphorylation, IκBα degradation, p65 phosphorylation, nuclear translocation,and acylation. It downregulates the NF-κB-regulated gene products like FLIP, cyclinD1, TRAF1, COX2, Bfl-1/A1, MMP-9, Bcl-xL, ICAM-1, Bcl-2, c-myc, XIAP,survivin, IAP1, and IAP2, and thus, it potentiates apoptosis (Murakami et al. 2002;Sakinah et al. 2007).

References

1) Leu et al. (2009), A small molecule inhibitor of inducible heat shock protein 70; Mol. Cell, 36 15 2) Abdelwahab et al. (2011), Zerumbone induces apoptosis in T-acute lymphoblastic leukemia cells; Leuk. Res., 35 268

zerumbone Preparation Products And Raw materials

Raw materials

Preparation Products

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zerumbone Suppliers

TargetMol Chemicals Inc.
Tel
+1-781-999-5354 +1-00000000000
Email
marketing@targetmol.com
Country
United States
ProdList
32165
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58
Aladdin Scientific
Tel
+1-+1(833)-552-7181
Email
sales@aladdinsci.com
Country
United States
ProdList
57505
Advantage
58
TargetMol Chemicals Inc.
Tel
Email
support@targetmol.com
Country
United States
ProdList
38632
Advantage
58
Focus Biomolecules
Tel
--
Fax
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Email
sales@focusbiomolecules.com
Country
United States
ProdList
1284
Advantage
58
Cayman Chemical Company
Tel
--
Fax
--
Email
cayman@caymanchem.com
Country
United States
ProdList
6213
Advantage
81
United States Biological
Tel
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Email
chemicals@usbio.net
Country
United States
ProdList
6214
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80
Glentham Life Sciences Ltd
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--
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Email
info@glentham.com
Country
United States
ProdList
2026
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58
MedChemExpress
Tel
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Fax
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Email
sales@medchemexpress.com
Country
United States
ProdList
6398
Advantage
58
Riedel-de Haen AG
Tel
--
Fax
--
Country
United States
ProdList
6773
Advantage
87
LKT Laboratories, Inc.
Tel
--
Fax
--
Email
info@lktlabs.com
Country
United States
ProdList
2164
Advantage
64
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View Lastest Price from zerumbone manufacturers

Changsha Staherb Natural Ingredients Co., Ltd.
Product
Zerumbone; Zingiber zerumbe extract 471-05-6
Price
US $0.00/kg
Min. Order
1kg
Purity
≥98% HPLC
Supply Ability
1000kg
Release date
2022-09-19

471-05-6, zerumboneRelated Search:


  • zerumbone
  • (2E,6E,10E)-2,6,9,9-Tetramethyl-2,6,10-cycloundecatrien-1-one
  • ZeruMbone (6CI,7CI)
  • (2E,6E,10E)-2,6,9,9-tetramethylcycloundeca-2,6,10-trien-1-one
  • GIHNTRQPEMKFKO-SKTNYSRSSA-N
  • 2,6,10-Cycloundecatrien-1-one, 2,6,9,9-tetramethyl-, (2E,6E,10E)-
  • Zingiber zerumbe extract
  • (2E,6E,10E)-2,6,9,9-Tetramethylcycloundeca-2,6,10-trienone
  • Zerumbone-RM
  • 471-05-6