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Key Documents

SML0656

Sigma-Aldrich

Rocaglamide

≥96% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C29H31NO7
Numéro CAS:
84573-16-0
Poids moléculaire :
505.56
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥96% (HPLC)

Forme

film

Couleur

colorless

Conditions d'expédition

wet ice

Température de stockage

−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

Clé InChI

DAPAQENNNINUPW-IDAMAFBJSA-N

Description générale

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.

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

This compound is featured on the MAPKKKs page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
Soyoung Kim et al.
Anti-cancer agents in medicinal chemistry, 6(4), 319-345 (2006-07-18)
During the past few years, a group of cyclopenta[b]benzofurans from the plant genus Aglaia has received broad scientific attention as interesting natural product lead compounds with potential anticancer and insecticidal activities. Since the first cyclopenta[b]benzofuran derivative, rocaglamide, from Aglaia elliptifolia
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
Baudouin Gerard et al.
Journal of the American Chemical Society, 126(42), 13620-13621 (2004-10-21)
A unified biomimetic approach to the aglain-forbaglin-rocaglamide classes of natural products is reported. The approach involves photogeneration of oxidopyryliums via excited-state intramolecular proton transfer (ESIPT) of 3-hydroxyflavones followed by [3+2] dipolar cycloaddition to the aglain core. An alpha-ketol (acyloin) rearrangement
Rocaglamide-A Potentiates Osteoblast Differentiation by Inhibiting NF-?B Signaling.
Li A, et al.
Molecular Cell, 38(11), 941-941 (2015)
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Articles

MAPKKKs

The extracellular signal regulated kinase (ERK1 and ERK2) pathways are activated by mitogens and play an important role in controlling cell growth and differentiation.

MAPKKKs

The extracellular signal regulated kinase (ERK1 and ERK2) pathways are activated by mitogens and play an important role in controlling cell growth and differentiation.

MAPKKKs

The extracellular signal regulated kinase (ERK1 and ERK2) pathways are activated by mitogens and play an important role in controlling cell growth and differentiation.

MAPKKKs

The extracellular signal regulated kinase (ERK1 and ERK2) pathways are activated by mitogens and play an important role in controlling cell growth and differentiation.

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