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Rocaglamide

SIGMA/SML0656 - ≥96% (HPLC)

Synonym: (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

CAS Number: 84573-16-0
Empirical Formula (Hill Notation): C29H31NO7
Molecular Weight: 505.56
Linear Formula: C29H31NO7
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-SML0656-100UG 100 µg
 $396.00
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assay ≥96% (HPLC)
color colorless
form film
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
Quality Level 100 
shipped in wet ice
SMILES string N(C)(C)C(=O)[C@H]1[C@H]([C@@]2([C@@](Oc5c2c(cc(c5)OC)OC)([C@@H]1c4ccccc4)c3ccc(cc3)OC)O)O
storage temp. −20°C
Application: Rocaglamide has been used as an anticancer drug to treat enterovirus 71 neuropathogenesis and to study the role of prohibitin.
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.
Biochem/physiol Actions: Rocaglamide is a potent anticancer agent.
Biochem/physiol Actions: Rocaglamide is associated with osteoblast differentiation. In rheumatoid arthritis, rocaglamide might suppress inflammation, by preventing the expression of cytokines involved in it.
Features and Benefits: This compound is featured on the MAPKKKs  page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here .
General description: Rocaglamide is known to be derived from tetrahydro benzofuran and is also an active chemical compound of Aglaia plants.
Packaging: 100 μg in glass bottle
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity ≥96% (HPLC)
Storage Temp. −20°C
UNSPSC 12352200

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