ROCAGLAMIDE

ChemicalBook > CAS DataBase List > ROCAGLAMIDE

Product Name: ROCAGLAMIDE
CAS No.: 84573-16-0
Chemical Name: ROCAGLAMIDE
Synonyms: Roc-A;NSC 326408;ROCAGLAMIDE;Rocaglamide A;NF-κB,Nuclear factor-kappaB,Heat shock proteins,inhibit,Rocaglamide,Eukaryotic Initiation Factor (eIF),Nuclear factor-κB,HSP,Inhibitor;N,N-Dimethyl-1α,8bβ-dihydroxy-6,8-dimethoxy-3β-phenyl-3aβ-(4-methoxyphenyl)-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2α-carboxamide;2,3,3a,8b-Tetrahydro-N,N-dimethyl-1α,8bβ-dihydroxy-6,8-dimethoxy-3β-phenyl-3aβ-(4-methoxyphenyl)-1H-cyclopenta[b]benzofuran-2α-carboxamide;2,3,3a,8b-Tetrahydro-1α,8bβ-dihydroxy-6,8-dimethoxy-3aβ-(4-methoxyphenyl)-N,N-dimethyl-3β-phenyl-1H-cyclopenta[b]benzofuran-2α-carboxamide;(1R)-N,N-Dimethyl-1α,8bβ-dihydroxy-3β-phenyl-3aβ-(4-methoxyphenyl)-6,8-dimethoxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2α-carboxamide;(1R)-2,3,3a,8b-Tetrahydro-1α,8bβ-dihydroxy-6,8-dimethoxy-3aβ-(4-methoxyphenyl)-N,N-dimethyl-3β-phenyl-1H-cyclopenta[b]benzofuran-2α-carboxamide
CBNumber: CB7847527
Molecular Formula: C29H31NO7
Formula Weight: 505.56
MOL File: 84573-16-0.mol

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ROCAGLAMIDE Property

Melting point:: 117-118 °C
Boiling point:: 667.3±55.0 °C(Predicted)
Density: 1.321±0.06 g/cm3(Predicted)
storage temp.: -20°C
solubility: Soluble in DMSO or Ethanol
pka: 11.70±0.70(Predicted)
form: film
color: colorless
Stability:: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month. Protect from exposure to light and moisture.

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Safety

WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

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

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML0656
Product name: Rocaglamide
Purity: ≥96% (HPLC)
Packaging: 100μg
Price: $360
Updated: 2024/03/01

Cayman Chemical

Product number: 14841
Product name: Rocaglamide
Purity: ≥95%
Packaging: 500μg
Price: $101
Updated: 2024/03/01

Cayman Chemical

Product number: 14841
Product name: Rocaglamide
Purity: ≥95%
Packaging: 1mg
Price: $152
Updated: 2024/03/01

TRC

Product number: R639450
Product name: Rocaglamide
Packaging: 1mg
Price: $500
Updated: 2021/12/16

Usbiological

Product number: R2997-90
Product name: Rocaglamide
Packaging: 100ug
Price: $601
Updated: 2021/12/16

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ROCAGLAMIDE Chemical Properties,Usage,Production

Description

Rocaglamide is an anti-inflammatory, insecticidal, and anticancer tetrahydrobenzofuran isolated from Aglaia species. It has been shown to inhibit both TNF-α and the activation of NF-κB in Jurkat T cells with IC₅₀ values in the nanomolar range. At 25 nM, rocaglamide induces apoptosis in various human leukemia cell lines, activating p38 MAPK/JNK and suppressing ERK. Rocaglamide also reduces IFN-γ, TNF-α, IL-2, and IL-4 production in peripheral blood T cells at a concentration of 50 nM. Furthermore, rocaglamide can inhibit the T cell expression of the immune response transcription factor, nuclear factor of activated T cells.

Uses

Rocaglamide is derived from a Chinese medicinal plant Aglaia. Rocaglamide induces apoptosis in various human leukemia cell lines and in acute lymphoblastic leukemia, chronic myeloid leukemia and acute myeloid leukemia cells freshly isolated from patients.

Definition

ChEBI: An organic heterotricyclic compound that is 2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan substituted by hydroxy groups at positions 1 and 8b, methoxy groups at positions 6 and 8, a 4-methoxyphenyl group at position 3a, a phenyl group at position 3 and a N,N-dimethylcarbamoyl group at position 1. Isolated from Aglaia odorata and Aglaia duperreana, it exhibits antineoplastic activity.

General Description

Rocaglamide is known to be derived from tetrahydro benzofuran and is also an active chemical compound of Aglaia plants.

Biochem/physiol Actions

Rocaglamide is a potent anticancer agent isolated from the genus Aglaia. Rocaglamides inhibit protein synthesis without affecting DNA or RNA synthesis. Recent study shows that Rocaglamide binds to prohibitin (PHB) 1 and 2, which prevents interaction between PHB and CRaf and inhibits CRaf activation and subsequently CRaf-MEK-ERK signaling. Also, Rocaglamide is an immunosuppressant that inhibits activation of NF-kB and NF-AT.

target

Bcl-2/Bax | Caspase | p53 | TNF-α | NF-kB | MEK | ERK | Chk | Raf | p38MAPK

References

1) Baumann?et al.?(2002),?Rocaglamide Derivatives Are Potent Inhibitors of NF-kB Activation in T-cells; J. Biol. Chem.?277?44791 2) Prolsch?et al.?(2005),?Rocaglamide Derivatives Are Immunosuppressive Phytochemicals That Target NF-AT Activity in T Cells; J. Immunol.?174?7075 3) Polier?et al.?(2012),?The natural anticancer compounds rocaglamides inhibit the Raf-MEK-ERK pathway by targeting prohibitin1 and 2; Chem. Biol.?19?1093 4) Neumann?et al.?(2014),?The natural anticancer compound rocaglamide selectively inhibits the G1-S phase transition in cancer cells through the ATM/ATR-mediated Chk1/2 cell cycle checkpoints; Int. J. Cancer?134?1991 5) Zhu?et al.?(2007),?The traditional Chinese herbal compound rocaglamide preferentially induces apoptosis in leukemia cells by modulation of mitogen-activated protein kinase activities; Int. J. Cancer?121?1839

ROCAGLAMIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from ROCAGLAMIDE manufacturers

Career Henan Chemical Co

Product: ROCAGLAMIDE 84573-16-0
Price: US $1.00/KG
Min. Order: 1KG
Purity: 98% HPLC
Supply Ability: 10 tons
Release date: 2020-03-12

84573-16-0, ROCAGLAMIDERelated Search:

HELENALIN 5-Aminosalicylic acid BAY 11-7085 Ceramides SU 4312 BAY 11-7082 WITHAFERIN A 6-AMINO-4-(4-PHENOXYPHENYLETHYLAMINO)QUINAZOLINE 3'-Hydroxyrocaglamide panepoxydone Rocaglamide I 2,3-DIPHENYL-2,3-BUTANEDIOL ROCAGLAMIDE (+/-)-HYDROBENZOIN (R,R)-(+)-HYDROBENZOIN 1-PHENYL-1-CYCLOPENTANOL LL 248 1-(4-Methoxyphenyl)-2-methylpropane-1,2-diol.

ROCAGLAMIDE

(1R)-2,3,3a,8b-Tetrahydro-1α,8bβ-dihydroxy-6,8-dimethoxy-3aβ-(4-methoxyphenyl)-N,N-dimethyl-3β-phenyl-1H-cyclopenta[b]benzofuran-2α-carboxamide

(1R)-N,N-Dimethyl-1α,8bβ-dihydroxy-3β-phenyl-3aβ-(4-methoxyphenyl)-6,8-dimethoxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2α-carboxamide

2,3,3a,8b-Tetrahydro-1α,8bβ-dihydroxy-6,8-dimethoxy-3aβ-(4-methoxyphenyl)-N,N-dimethyl-3β-phenyl-1H-cyclopenta[b]benzofuran-2α-carboxamide

2,3,3a,8b-Tetrahydro-N,N-dimethyl-1α,8bβ-dihydroxy-6,8-dimethoxy-3β-phenyl-3aβ-(4-methoxyphenyl)-1H-cyclopenta[b]benzofuran-2α-carboxamide

N,N-Dimethyl-1α,8bβ-dihydroxy-6,8-dimethoxy-3β-phenyl-3aβ-(4-methoxyphenyl)-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2α-carboxamide

(1R,2R,3S,3aR,8bS)-2,3,3a,8b-Tetrahydro-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-1H-cyclopenta[b]benzofuran-2-carboxamide

NSC 326408

Roc-A

Rocaglamide A

1H-Cyclopenta[b]benzofuran-2-carboxamide, 2,3,3a,8b-tetrahydro-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-, (1R,2R,3S,3aR,8bS)-

(1R,2R,3S,3aR,8bS)-1,8b-Dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxamide

NF-κB,Nuclear factor-kappaB,Heat shock proteins,inhibit,Rocaglamide,Eukaryotic Initiation Factor (eIF),Nuclear factor-κB,HSP,Inhibitor

84573-16-0