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ROCAGLAMIDE

ROCAGLAMIDE Structure
ROCAGLAMIDE structure
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
Molecular Weight:
505.56
MDL Number:
MFCD08702699
MOL File:
84573-16-0.mol
MSDS File:
SDS
Last updated:2024-11-14 14:09:35
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ROCAGLAMIDE Properties

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
form film
pka 11.70±0.70(Predicted)
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.
FDA UNII FRG4N852F7

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P305+P351+P338
WGK Germany  3

ROCAGLAMIDE price More Price(28)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SML0656 Rocaglamide ≥96% (HPLC) 84573-16-0 100μg $360 2024-03-01 Buy
Cayman Chemical 14841 Rocaglamide ≥95% 84573-16-0 500μg $101 2024-03-01 Buy
Cayman Chemical 14841 Rocaglamide ≥95% 84573-16-0 1mg $152 2024-03-01 Buy
TRC R639450 Rocaglamide 84573-16-0 1mg $500 2021-12-16 Buy
Usbiological R2997-90 Rocaglamide 84573-16-0 100ug $601 2021-12-16 Buy
Product number Packaging Price Buy
SML0656 100μg $360 Buy
14841 500μg $101 Buy
14841 1mg $152 Buy
R639450 1mg $500 Buy
R2997-90 100ug $601 Buy

ROCAGLAMIDE Chemical Properties,Uses,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

ROCAGLAMIDE Suppliers

Global( 74)Suppliers
Supplier Tel Email Country ProdList Advantage
BOC Sciences 		+1-631-485-4226 inquiry@bocsci.com United States 19553 58
career henan chemical co 		+86-0371-86658258 +8613203830695 factory@coreychem.com China 29811 58
AFINE CHEMICALS LIMITED 		+86-0571-85134551 sales@afinechem.com China 15352 58
Alfa Chemistry 		Info@alfa-chemistry.com United States 24072 58
Nantong HI-FUTURE Biology Co., Ltd. 		+undefined18051384581 sales@chemhifuture.com China 3135 58
TargetMol Chemicals Inc. 		support@targetmol.com United States 38632 58
Wuhan Topule Biopharmaceutical Co., Ltd 		+8618327326525 masar@topule.com China 8467 58
Shanghai Acmec Biochemical Technology Co., Ltd. 		+undefined18621343501 product@acmec-e.com China 33338 58
Aladdin Scientific 		+1-+1(833)-552-7181 sales@aladdinsci.com United States 52925 58
SHANGHAI KEAN TECHNOLOGY CO., LTD. 		+8613817748580 cooperation@kean-chem.com China 40066 58
Supplier Advantage
BOC Sciences 		58
career henan chemical co 		58
AFINE CHEMICALS LIMITED 		58
Alfa Chemistry 		58
Nantong HI-FUTURE Biology Co., Ltd. 		58
TargetMol Chemicals Inc. 		58
Wuhan Topule Biopharmaceutical Co., Ltd 		58
Shanghai Acmec Biochemical Technology Co., Ltd. 		58
Aladdin Scientific 		58
SHANGHAI KEAN TECHNOLOGY CO., LTD. 		58

View Lastest Price from ROCAGLAMIDE manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Rocaglamide pictures 2024-11-14 Rocaglamide
84573-16-0
 US $299.00 / mg 98.46% 10g TargetMol Chemicals Inc.
ROCAGLAMIDE pictures 2020-03-13 ROCAGLAMIDE
84573-16-0
 US $1.00 / KG 1KG 98% HPLC 10 tons Career Henan Chemical Co
  • Rocaglamide pictures
  • Rocaglamide
    84573-16-0
  • US $299.00 / mg
  • 98.46%
  • TargetMol Chemicals Inc.
  • ROCAGLAMIDE pictures
  • ROCAGLAMIDE
    84573-16-0
  • US $1.00 / KG
  • 98% HPLC
  • Career Henan Chemical Co

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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