471-05-6

Basic information

• Product Name: zerumbone
• Synonyms: 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
• CAS NO: 471-05-6
• Molecular Formula: C₁₅H₂₂O
• Molecular Weight: 218.33
• Mol File: 471-05-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 67-69℃
• Boiling Point: 321.611 °C at 760 mmHg
• Flash Point: 133.945 °C
• Appearance: white to off-white/
• Density: 0.888 g/cm³
• Vapor Pressure: 0.000295mmHg at 25°C
• Refractive Index: 1.468
• Storage Temp.: 2-8°C
• Solubility: DMSO: ≥10mg/mL
• 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.
• CAS DataBase Reference: zerumbone(CAS DataBase Reference)
• NIST Chemistry Reference: zerumbone(471-05-6)
• EPA Substance Registry System: zerumbone(471-05-6)

Safety Data

• Hazard Codes: Xi,N
• Statements: 43-50
• Safety Statements: 36/37-60-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 471-05-6(Hazardous Substances Data)

Usage

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 preventiontreatment 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

InChI:InChI=1/C15H22O/c1-12-6-5-7-13(2)14(16)9-11-15(3,4)10-8-12/h7-9,11H,5-6,10H2,1-4H3/b11-9+,12-8+,13-7+

Upstream product

• 17678-70-5 Zerumbol 
• 17678-70-5 zerumbol 
• 79729-85-4 (5E,9E)-(1S,11S)-1,5,8,8-Tetramethyl-12-oxa-bicyclo[9.1.0]dodeca-5,9-dien-2-one 
• 79729-84-3 (5E,9E)-(1R,2S,11S)-1,5,8,8-Tetramethyl-12-oxa-bicyclo[9.1.0]dodeca-5,9-dien-2-ol 
• 108101-44-6 (1S,2S)-1,2-epoxyhumulene 
• 79729-83-2 (2Z,4E,8E)-(S)-2,6,6,9-Tetramethyl-cycloundeca-2,4,8-trienol 

Downstream Products

• 22471-70-1 (+/-)-(6R,7R)-epoxy-2,6,9,9-tetramethyl-2,10-cycloundecadien-1-one 

Relevant articles and documents

Br?nsted acid-induced transannulation of the phytochemical zerumbone

The sesquiterpene zerumbone was treated with HCl in ethyl acetate under the light-protected condition, and the time-dependent conversions were analyzed by gas chromatography. Nine products were isolated, and their structures were revealed by several NMR m

The chemistry of zerumbone. Part 5: Structural transformation of the dimethylamine derivatives

Zerumbone (1) and its 6,7-epoxide (2) react with ammonia and dimethylamine regio- and stereospecifically, affording monoamines 3, 4, 7 and 8. All adducts have the same relative configuration at C2 and C3. The conjugate amination is thermodynamically controlled to arrive at a single diastereomer. At 15°C 7 reacts with cyanide to give aminonitrile 10 as the single product, while at 30°C, acyclic aminonitrile 11 is also formed. The reaction with 8 affords at 0°C bicyclic aminonitrile 12 of the asteriscane skeleton, while at 30°C or higher temperature, mixtures of 12 and tricyclic nitriles 13 and 13′ are obtained. Refluxing of 7, 8 and 10 in aqueous acetonitrile promotes scission of the zerumbone ring by retro-Mannich reaction to provide acyclic aldehydes 16-18, respectively. The dimethylamino group of 7, 8 and 10 is eliminated stereospecifically by Cope- and base-catalyzed eliminations to regenerate the zerumbone skeleton in the products 1, 2 and 21. Cope elimination of 12 results in a mixture of 13 and 13′ by deaminative transannular etherification.

CONVERSION OF HUMULENE TO ZERUMBONE

Humulene was first converted to zerumbone through a sequence of chemical reactions.