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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;12a-DEOXYTEPHROSIN;Deguelin, 10 mM in DMSO;(-)-Deguelin, Akt inhibitor
CBNumber
CB9431676
Molecular Formula
C23H22O6
Formula Weight
394.42
MOL File
522-17-8.mol
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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.
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Safety

Safety Statements 
22-24/25
WGK Germany 
3
RTECS 
DX1500000
HS Code 
29329990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

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

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

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
D0817
Product name
(?)-Deguelin
Purity
>98% (HPLC), powder
Packaging
5mg
Price
$250.8
Updated
2025/07/31
TCI Chemical
Product number
D5646
Product name
(-)-Deguelin
Packaging
50MG
Price
$407
Updated
2025/07/31
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
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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.

Synthesis

70191-71-8

522-17-8

Synthesis of (7aS,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-9-hydroxy-2,3-dimethoxy-8-(3-methyl-2-buten-1-yl)[1]benzopyrano[3,4-B][1]benzopyridoxol-12(6H)-ones as (6AS,12AS)-6A,12A-dihydropyrano[2,4-B][1]benzopyridoxol-12(6H)-ones 3H-pyrano[2,3-c:6,5-f']dibenzopyran-7(7aH)-one in the following general steps: 1. phenylselenyl chloride (68 mg, 0.35 mmol) was added under argon protection to an anhydrous dichloromethane containing (6AS,12AS)-6A,12A-dihydro-9-hydroxy-2,3-dimethoxy-8-(3-methyl-2-buten-1-yl)[1 ]benzopyrano[3,4-B][1 ]benzopyridoxol-12(6H)-one (128 mg, 0.32 mmol) in an anhydrous dichloromethane solution (4.0 mL) at a reaction temperature of -30 °C with stirring for 10 min. 2. Slowly warm to room temperature and continue stirring for 2 hours followed by 1 hour. 3. remove the solvent under pressure, dissolve the residue in tetrahydrofuran (4.0 mL) and add 30% aqueous hydrogen peroxide solution (0.06 mL) at 0 °C. 4. The reaction mixture was stirred to room temperature, during which the progress of the reaction was monitored by thin layer chromatography (TLC). 5. Upon completion of the reaction, the organic layer was separated by adding ethyl acetate (8.0 mL) and water (4.0 mL). 6. The organic layer was washed sequentially with 5% aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered and concentrated. 7. The crude product was purified by fast column chromatography (ethyl acetate:hexane=1:2) to afford (7aS,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-pyrano[2,3-c:6,5-f']dibenzopyran-7(7aH)-one in the form of a yellowish solid in a yield of 61% (78 mg). Product characterization data: 1H-NMR (CDCl3, 400 MHz) δ 7.72 (d, 1H, J = 8.7 Hz), 6.77 (s, 1H), 6.62 (d, 1H, J = 10.0 Hz), 6.43 (s, 1H), 6.43 (d, 1H, J = 8.7 Hz), 5.53 (d, 1H, J = 10.0 Hz), 4.89 (m, 1H ), 4.61 (dd, 1H, J = 12.0, 3.1 Hz), 4.17 (d, 1H, J = 12.0 Hz), 3.82 (d, 1H, J = 4.1 Hz), 3.78 (s, 3H), 3.75 (s, 3H), 1.43 (s, 3H), 1.36 (s, 3H). 13C-NMR (CDCl3, 100 MHz) δ 189.2, 160.0, 156.9, 149.4, 147.4, 143.8, 128.6, 128.5, 115.7, 112.7, 111.4, 110.4, 109.1, 104.7, 100.9, 77.6, 72.4, 66.2, 56.3, 55.8, 44.3, 28.4, 28.1. HRMS (FAB) calculated value C23H23O6 (M+H+): 395.1495, measured: 395.1495.

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] KYUNG-HEE CHUN. Effects of deguelin on the phosphatidylinositol 3-kinase/Akt pathway and apoptosis in premalignant human bronchial epithelial cells.[J]. JNCI Journal of the National Cancer Institute, 2003, 95 4: 291-302. DOI:10.1093/jnci/95.4.291
[2] HYOUN WOO KANG. Deguelin, an Akt inhibitor, down-regulates NF-κB signaling and induces apoptosis in colon cancer cells and inhibits tumor growth in mice.[J]. Digestive Diseases and Sciences, 2012, 57 11: 2873-2882. DOI:10.1007/s10620-012-2237-x
[3] LEE H Y. Molecular mechanisms of deguelin-induced apoptosis in transformed human bronchial epithelial cells[J]. Biochemical pharmacology, 2004, 68 6: Pages 1119-1124. DOI:10.1016/j.bcp.2004.05.033
[4] CHIHIRO ITO. Cancer chemopreventive activity of rotenoids from Derris trifoliata.[J]. Planta medica, 2004, 70 6: 585-588. DOI:10.1055/s-2004-815447

DEGUELIN Preparation Products And Raw materials

Raw materials

Preparation Products

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DEGUELIN Suppliers

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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

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  • (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...
  • (-)-Deguelin, Akt inhibitor
  • Deguelin, 10 mM in DMSO
  • 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