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Sigma-Aldrich

Rocaglamide

≥96% (HPLC)

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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
Empirical Formula (Hill Notation):
C29H31NO7
CAS Number:
84573-16-0
Molecular Weight:
505.56
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥96% (HPLC)

form

film

color

colorless

shipped in

wet ice

storage temp.

−20°C

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

General description

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

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 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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Prohibitin plays a critical role in Enterovirus 71 neuropathogenesis.
Too I H K, et al.
PLoS Pathogens, 14(1), e1006778-e1006778 (2018)
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
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
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
C Schneider et al.
Phytochemistry, 54(8), 731-736 (2000-10-03)
Bark of Aglaia spectabilis collected on the island of Phu Quoc (Vietnam) yielded insecticidal cyclopentatetrahydrobenzofurans of the rocaglamide type including four new natural products. Structure elucidation of the new compounds is described. All rocaglamide derivatives isolated exhibited strong insecticidal activity
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