ROCAGLAMIDE

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For Research Use Only.

Size	Price	Stock	Quantity
1 mg	$519	In stock

Category

Alkaloids

Cat.No.

NP0466

CAS

84573-16-0

Product Name

ROCAGLAMIDE

Structure

Product Details

Description

Rocaglamide is the first cyclopenta[b]benzofuran derivative extracted from Aglaia elliptifolia in 1982 by King and colleagues. Its IC50 value is ~50 nM for the heat shock reporter. It has antileukemic activity and displays potent insecticidal, antifungal, anti-inflammatory and anticancer activities. It is an immunosuppressant that inhibits activation of NF-kB and NF-AT. It markedly inhibited tumor growth from Huh-7 cells propagated in severe combined immunodeficient mice. It induces apoptosis in various human leukemia cell lines and in acute lymphoblastic leukemia, chronic myeloid leukemia and acute myeloid leukemia cells. It inhibit protein synthesis without affecting DNA or RNA synthesis.

Synonyms

Rocaglamide; Rocaglamide A; RocA; NSC 326408. (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;1H-Cyclopenta(b)benzofuran-2-carboxamide, 2,3,3a,8b-tetrahydro-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-, (1R,2R,3S,3aR,8bS)-;[1R-(1α,2α,3β,3aβ,8bβ)]-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

IUPAC Name

(1R,2R,3S,3aR,8bS)-1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-2-carboxamide

Molecular Weight

505.56

Molecular Formula

C29H31NO7

Canonical SMILES

CN(C)C(=O)C1C(C2(C(C1O)(C3=C(C=C(C=C3O2)OC)OC)O)C4=CC=C(C=C4)OC)C5=CC=CC=C5

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

InChIKey

DAPAQENNNINUPW-IDAMAFBJSA-N

Boiling Point

667.3±55.0 °C | Condition: Press: 760 Torr

Melting Point

117-118 °C

Purity

95%

Density

1.321±0.06 g/cm3 | Condition: Temp: 20 °C Press: 760 Torr

Solubility

10 mM in DMSO

Appearance

Solid powder

Application

Rocaglamide has antileukemic activity and displays potent insecticidal, antifungal, anti-inflammatory and anticancer activities. It is an immunosuppressant that inhibits activation of NF-kB and NF-AT. It inhibit protein synthesis without affecting DNA or RNA synthesis.

Shelf Life

2 month in rt, long time

Storage

-20°C Freezer

Color

Colorless

Definition

ChEBI: An organic heterotricyclic compound that is 2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan substituted by hydroxy groups at positions 1 and 8b, methoxy groups at positions 6 and 8, a 4-methoxyphenyl group at
position 3a, a phenyl group at position 3 and a N,N-dimethylcarbamoyl group at position 1. Isolated from Aglaia odorata and Aglaia duperreana, it exhibits antineoplastic activity.

Form

Film

NACRES

NA.77

Packaging

1 mg

pKa

11.70±0.70(Predicted)

Quality Level

100

Stability

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month. Protect from exposure to light and moisture.

Uses

Rocaglamide is derived from a Chinese medicinal plant Aglaia. 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.

WGK Germany

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