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;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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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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(-)-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)

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Antitumour