ChemicalBook > CAS DataBase List > DEGUELIN

DEGUELIN

Product Name
DEGUELIN
CAS No.
522-17-8
Chemical Name
DEGUELIN
Synonyms
DEGUELIN;Ccris 8104;()-Deguelin;(-)-DEGUELIN;(7as-cis)-oxy-;Deguelin (6CI);(-)-cis-Deguelin;(-)-cis-Deguelin;12a-DEOXYTEPHROSIN;(-)-DEGUELIN;(-)-CIS-DEGUELIN
CBNumber
CB9431676
Molecular Formula
C23H22O6
Formula Weight
394.42
MOL File
522-17-8.mol
More
Less

DEGUELIN Property

Melting point:
85-87 °C(lit.)
alpha 
D27 -97.2° (c = 0.2 in benzene)
Boiling point:
560.1±50.0 °C(Predicted)
Density 
1?+-.0.06 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
DMSO: >10 mg/mL
form 
solid
color 
white to yellow
optical activity
[α]/D -70 to -80°, c = 0.2 in methanol
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
More
Less

Safety

Safety Statements 
22-24/25
WGK Germany 
3
RTECS 
DX1500000
HS Code 
29329990
More
Less

Hazard and Precautionary Statements (GHS)

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
D0817
Product name
(?)-Deguelin
Purity
>98% (HPLC), powder
Packaging
5mg
Price
$257
Updated
2024/03/01
Cayman Chemical
Product number
10010706
Product name
(?)-Deguelin
Purity
≥98%
Packaging
5mg
Price
$55
Updated
2024/03/01
Cayman Chemical
Product number
10010706
Product name
(?)-Deguelin
Purity
≥98%
Packaging
10mg
Price
$105
Updated
2024/03/01
Cayman Chemical
Product number
10010706
Product name
(?)-Deguelin
Purity
≥98%
Packaging
25mg
Price
$248
Updated
2024/03/01
Cayman Chemical
Product number
10010706
Product name
(?)-Deguelin
Purity
≥98%
Packaging
50mg
Price
$440
Updated
2024/03/01
More
Less

DEGUELIN Chemical Properties,Usage,Production

Description

Rotenoids, deriving from the flavonoid family of compounds, act as chemopreventive agents that inhibit NADH:ubiquinone oxidoreductase activity and suppress phorbol ester-induced ornithine decarboxylase (ODC) activity. The rotenoid compound deguelin, originally isolated from the bark of M. sericea (Leguminosae) to be used as an insecticide and fish poison, has chemopreventive and chemosensitizing effects in models of skin, mammary, colon, and lung carcinogenesis. Deguelin inhibits cell growth (IC50 = <10-8 M), blocks PI3K/Akt activation, suppresses COX-2 expression, and induces apoptosis in premalignant and squamous human bronchial epithelial (HBE) cells without affecting normal HBE cells. At 6 mg/kg, deguelin induces Parkinson’s disease-like symptoms in rats after six days of subcutaneous infusion and therefore may also serve as a useful model for Parkinson’s disease research.

Uses

antineoplastic, antiviral, insecticide, ornithine decarboxylate inhibitor

Uses

(?)-Deguelin has been used as:

  • a nicotinamide adenine dinucleotide hydrogen (NADH) dehydrogenase (Complex I) inhibitor to study its effects on mitochondrial respiratory inhibition in human hepatocarcinoma cells (HepG2) and human renal proximal tubule epithelial cells (RPTECs)
  • an antiviral compound to study inhibitory effects on human cytomegalovirus (HCMV)-infected human foreskin fibroblast (HFF) cells
  • an analytical standard in high-performance liquid chromatography (HPLC)

Uses

Deguelin exhibits potent apoptotic and antiangiogenic activities in a variety of transformed cells and cancer cells. Deguelin also exhibits potent tumor suppressive effects in xenograft tumor models for many human cancers.

Definition

ChEBI: Deguelin is a rotenone that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted by methoxy groups at positions 9 and 10, and by two methyl groups at position 3 (the 7aS,13aS-stereoisomer). It exists in abundant quantities in the bark, roots, and leaves of the Leguminosae family of plants and reported to exert anti-tumour effects in various cancers. It has a role as an apoptosis inducer, an antineoplastic agent, a plant metabolite, an angiogenesis inhibitor, an antiviral agent, a mitochondrial NADH:ubiquinone reductase inhibitor, an anti-inflammatory agent and an EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor. It is a member of rotenones, an aromatic ether, an organic heteropentacyclic compound and a diether.

Biological Activity

Anticancer and antiviral agent; chemopreventive and pro-apoptotic. Inhibits phorbol ester-induced ornithine decarboxylase and NADH:ubiquinone oxidoreductase activities (IC 50 values are 11 and 6.9 nM respectively). Inhibits PI 3-kinase and reduces pAkt levels in pre-malignant and malignant human bronchial epithelial cells. Active in vivo .

Biochem/physiol Actions

Deguelin is a natural rotenoid compound present abundantly in barks, leaves, seeds, and roots of the plants belonging to the Leguminosae family. Deguelin has been studied as a therapeutic agent against the skin, lung cancer, and mammary tumorigenesis.

target

FAK | ROS | Caspase | Akt | ERK | PARP | EGFR | p53 | p21 | MMP(e.g.TIMP) | PKC | PI3K | MEK | NOS | COX | JNK | p38MAPK | ROCK | NF-kB | p65 | VEGFR

References

1) Chun et al. (2003), Effects of deguelin on the phosphatidylinositol 3- kinase/Akt pathway and apoptosis in premalignant human bronchial epithelial cells; J. Natl. Cancer Inst., 95 291 2) Kang et al. (2012), Deguelin, an AKT Inhibitor, Down-Regulates NFκB Signaling and Induces Apoptosis in Colon Cancer Cells and Inhibits Tumor Growth in Mice; Dig. Dis. Sci.,?57 2873 3) Lee et al. (2004), Molecular mechanisms of deguelin-induced apoptosis in transformed human bronchial epithelial cells; Biochem. Pharmacol., 68 1119 4) Ito et al. (2004), Cancer chemopreventive activity of rotenoids from Derris trifoliata; Planta Med., 70 8

DEGUELIN Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

DEGUELIN Suppliers

Canada 1 China 130 Europe 1 Germany 2 India 2 Japan 2 Switzerland 2 United Kingdom 3 United States 17 Global 160
Shanghai Rechem science Co., Ltd.
Tel
21-31433387 15618786686
Fax
QQ:1369748377
Email
sales@rechemscience.com
Country
China
ProdList
2990
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
Advantage
69
Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
Advantage
61
Spectrum Chemical Manufacturing Corp.
Tel
021-021-021-67601398-809-809-809 15221380277
Fax
021-57711696
Email
marketing_china@spectrumchemical.com
Country
China
ProdList
9658
Advantage
60
BioBioPha Co., Ltd.
Tel
0871-65217109 13211707573;
Fax
0871-65215563
Email
y.liu@mail.biobiopha.com
Country
China
ProdList
5653
Advantage
65
Shanghai T&W Pharmaceutical Co., Ltd.
Tel
+86 21 61551611
Fax
+86 21 50676805
Country
China
ProdList
9891
Advantage
58
Haoyuan Chemexpress Co., Ltd.
Tel
021-58950125
Fax
(86) 21-58955996
Email
info@chemexpress.com
Country
China
ProdList
7552
Advantage
61
TOKYO CHEMICAL INDUSTRY CO., LTD.
Tel
03-36680489
Fax
03-3668-0520
Email
Sales-JP@TCIchemicals.com
Country
Japan
ProdList
28387
Advantage
80
TCI Europe
Tel
320-37350700
Fax
+32 (0)37350701
Email
sales@tcieurope.eu
Country
Europe
ProdList
23671
Advantage
75
More
Less

View Lastest Price from DEGUELIN manufacturers

Career Henan Chemical Co
Product
Deguelin 522-17-8
Price
US $1.00/g
Min. Order
1g
Purity
99%
Supply Ability
1ton
Release date
2020-01-10

522-17-8, DEGUELINRelated Search:

NS-398 Indometacin Piroxicam (S)-(+)-Ibuprofen Saw Palmetto P.E Heartleaf Houttuynia P.E. Meloxicam Elm bark extract Rotenone N-(2-PHENYLETHYL)-INDOMETHACIN AMIDE Equol DEGUELIN 4'-METHOXY-2-P-METHOXYPHENYLBUTYROPHENONE 1-(2,4-Dihydroxyphenyl)-2-(3,4-dimethoxyphenyl)ethanone 2,5-DIMETHOXYPHENYLACETONE METHYLEUGENOLGLYCOL 5-HYDROXY-2,2-DIMETHYL-2H-CHROMENE-6-CARBALDEHYDE (2,4,5-TRIMETHOXYPHENYL)ACETALDEHYDE

  • (7as-cis)-oxy-
  • 3h-bis(1)benzopyrano(3,4-b:6’,5’-e)pyran-7(7ah)-one,13,13a-dihydro-9,10-dimeth
  • (7AS,13AS)-13,13A-DIHYDRO-9,10-DIMETHOXY-3,3-DIMETHYL-3H-BIS[1]BENZOPYRANO[3,4-B:6',5'-E]PYRAN-7(7AH)-ONE
  • (-)-DEGUELIN
  • DEGUELIN
  • (7aS,13aS)-13,13a-Dihydro-9,10-dimethoxy-3,3-dimethyl-(3H)-bis[1]benzopyrano[3.4-b.6'.5'-e]pyran-7(7aH)-one
  • (7aS)-3,3-Dimethyl-9,10-dimethoxy-7,7aα,13,13aα-tetrahydro-3H-bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7-one
  • 3,3-Dimethyl-9,10-dimethoxy-7,7aα,13,13aα-tetrahydro-3H-bis[1]benzopyrano[3,4-b:6',5'-e]pyran-7-one
  • 3H-Bis(1)benzopyrano(3,4-B:6',5'-E)pyran-7(7ah)-one, 13,13A-dihydro-9,10-dimethoxy-3,3-dimethyl-, (7as,13as)-
  • 3H-Bis(1)benzopyrano(3,4-B:6',5'-E)pyran-7(7ah)-one, 13,13A-dihydro-9,10-dimethoxy-3,3-dimethyl-, (7as-cis)-
  • Ccris 8104
  • (-)-cis-Deguelin
  • Deguelin (6CI)
  • 12a-DEOXYTEPHROSIN
  • (-)-DEGUELIN;(-)-CIS-DEGUELIN
  • ()-Deguelin
  • (7aS,13aS)-9,10-Dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-pyrano[2,3-c:6,5-f']dichromen-7(7aH)-one
  • (7aS,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chr...
  • (-)-cis-Deguelin
  • (7aS,13aS)-9,10-Dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-pyrano[2,3-c:6,5-f']dichromen-7(7aH)-one
  • 522-17-8
  • BioChemical
  • Cell Biology
  • Cell Signaling and Neuroscience
  • Kinase/Phosphatase Biology
  • Serine/Threonine Kinase Inhibitors
  • Protein Kinase B (Akt/PKB)
  • Miscellaneous Natural Products
  • Antitumour