Rocaglamide

• CAS: 84573-16-0
• Catalog Number: ACM84573160
• Category: Inhibitors
• Molecular Weight: 505.6
• Molecular Formula: C₂₉H₃₁NO₇
• Description: Rocaglamide (Roc-A) is isolated from the genus Aglaia and can be used for coughs, injuries, asthma and inflammatory skin diseases. Rocaglamide is a potent inhibitor of NF-κB activation in T-cells. Rocaglamide is a potent and selective heat shock factor 1 (HSF1) activation inhibitor with an IC50 of ~50 nM. Rocaglamide inhibits the function of the translation initiation factor eIF4A. Rocaglamide also has anticancer properties in leukemia.
• Synonyms: (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
• InChI: InChI=1S/C29H31NO7/c1-30(2)27(32)23-24(17-9-7-6-8-10-17)29(18-11-13-19(34-3)14-12-18)28(33,26(23)31)25-21(36-5)15-20(35-4)16-22(25)37-29/h6-16,23-24,26,31,33H,1-5H3/t23-,24-,26-,28+,29+/m1/s1
• InChI Key: DAPAQENNNINUPW-IDAMAFBJSA-N
• Melting Point: 117-118 °C
• Complexity: 810
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 5
• Exact Mass: 505.21005233
• Heavy Atom Count: 37
• Hydrogen Bond Acceptor Count: 7
• Hydrogen Bond Donor Count: 2
• Isomeric SMILES: CN(C)C(=O)[C@@H]1[C@H]([C@]2([C@@]([C@@H]1O)(C3=C(O2)C=C(C=C3OC)OC)O)C4=CC=C(C=C4)OC)C5=CC=CC=C5
• Monoisotopic Mass: 505.21005233
• Physical State: Powder
• Rotatable Bond Count: 6
• Topological Polar Surface Area: 97.7 Ų

Custom Q&A

What is the chemical formula of Rocaglamide?

The chemical formula of Rocaglamide is C29H31NO7.

What is the molecular weight of Rocaglamide?

The molecular weight of Rocaglamide is 505.56.

What is the melting point of Rocaglamide?

The melting point of Rocaglamide is 117-118 °C.

Where is Rocaglamide derived from?

Rocaglamide is derived from a Chinese medicinal plant Aglaia.

What are the uses of Rocaglamide?

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.

How does Rocaglamide inhibit the activation of NF-κB in Jurkat T cells?

Rocaglamide inhibits both TNF-α and the activation of NF-κB in Jurkat T cells with IC50 values in the nanomolar range.

What is the stability of Rocaglamide?

Rocaglamide is stable for 2 years from the date of purchase as supplied, and solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.

How does Rocaglamide reduce production of IFN-γ, TNF-α, IL-2, and IL-4 in peripheral blood T cells?

Rocaglamide reduces the production of these cytokines in peripheral blood T cells at a concentration of 50 nM.

What is the safety classification of Rocaglamide in Germany?

Rocaglamide is classified as WGK Germany 3.

How does Rocaglamide inhibit the Raf-MEK-ERK pathway?

Rocaglamide binds to prohibitin 1 and 2, preventing interaction between PHB and CRaf, inhibiting CRaf activation and subsequently CRaf-MEK-ERK signaling.