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Merck

SML0656

Rocaglamide

≥96% (HPLC), anti-cancer agent, film

Synonym(s):

(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

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About This Item

Empirical Formula (Hill Notation):
C29H31NO7
CAS Number:
84573-16-0
Molecular Weight:
505.56
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥96% (HPLC)
Form:
film
Quality level:
100

Key Documents

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Product Name

Rocaglamide, ≥96% (HPLC)

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

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

assay

≥96% (HPLC)

form

film

color

colorless

shipped in

wet ice

storage temp.

−20°C

Quality Level

100

Related Categories

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.
Rocaglamide is a potent anticancer agent.
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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000383537
0000383537
0000189946
0000189946
0000139551

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M Dreyer et al.
Journal of natural products, 64(4), 415-420 (2001-04-28)
Organic-soluble extracts of the twigs of Aglaia oligophylla collected in Vietnam yielded four insecticidal cyclopentatetrahydrobenzofurans of the rocaglamide type including one new natural product (compound 4). Moreover, two cyclopentatetrahydrobenzopyran derivatives, belonging to the aglain and aglaforbesin types, respectively, were also
Jia Y Zhu et al.
International journal of cancer, 121(8), 1839-1846 (2007-06-15)
With an increasing cancer rate worldwide, there is an urgent quest for the improvement of anticancer drugs. One of the main problems of present chemotherapy in treatment of tumor patients is the toxicity of drugs. Most of the existent anticancer
Prohibitin plays a critical role in Enterovirus 71 neuropathogenesis.
Too I H K, et al.
PLoS Pathogens, 14(1), e1006778-e1006778 (2018)
Matthew W Giese et al.
Organic letters, 10(19), 4215-4218 (2008-08-30)
The tricyclic core of the cyclopentabenzofurans has been prepared in an efficient and stereoselective manner utilizing an intramolecular silyl vinylketene formation/[4 + 1] annulation sequence. This novel approach affords the ABC ring system where the adjacent phenyl and aryl substituents
Baudouin Gerard et al.
Journal of the American Chemical Society, 128(24), 7754-7755 (2006-06-15)
Enantioselective syntheses of methyl rocaglate and the related natural products rocaglamide and rocaglaol are outlined. The approach involves enantioselective [3 + 2] photocycloaddition promoted by chiral Brønsted acids (TADDOLs) to afford an aglain precursor followed by a ketol shift/reduction sequence
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