Tracheloside

Inquiry

For Research Use Only.

Category

Lignans

Cat.No.

NP4208

CAS

33464-71-0

Product Name

Tracheloside

Structure

Product Details

Description

Tracheloside, was isolated from seeds of Carthamus tinctorius (Compositae) as an anti-estrogenic principle against cultured Ishikawa cells by employing a bioassay-linked HPLC-ELSD method. Tracheloside significantly decreased the activity of alkaline phosphatase (AP), an estrogen-inducible marker enzyme, with an IC(50) value of 0.31 microg/ml, a level of inhibition comparable to that of tamoxifen (IC(50) = 0.43 microg/ml).

Synonyms

(3S,4S)-4-[(3,4-Dimethoxyphenyl)methyl]-3-[[4-(β-D-glucopyranosyloxy)-3-methoxyphenyl]methyl]-4,5-dihydro-3-hydroxyfuran-2(3H)-one; (3S,4S)-4-[(3,4-Dimethoxyphenyl)methyl]-3-[[4-(beta-D-glucopyranosyloxy)-3-methoxyphenyl]methyl]dihydro-3-hydroxy-2(3H)-furanone; 2-Hydroxyarctiin; 2(3H)-Furanone,4-[(3,4-dimethoxyphenyl)methyl]-3-[[4-(b-D-glucopyranosyloxy)-3-methoxyphenyl]methyl]dihydro-3-hydroxy-,(3S,4S)-

IUPAC Name

(3S,4S)-4-[(3,4-dimethoxyphenyl)methyl]-3-hydroxy-3-[[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl]oxolan-2-one

Molecular Weight

550.2

Molecular Formula

C27H34O12

Canonical SMILES

COC1=C(C=C(C=C1)CC2COC(=O)C2(CC3=CC(=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)OC)O)OC

InChI

InChI=1S/C27H34O12/c1-34-17-6-4-14(9-19(17)35-2)8-16-13-37-26(32)27(16,33)11-15-5-7-18(20(10-15)36-3)38-25-24(31)23(30)22(29)21(12-28)39-25/h4-7,9-10,16,21-25,28-31,33H,8,11-13H2,1-3H3/t16-,21+,22+,23-,24+,25+,27-/m0/s1

InChIKey

LWYAMIUSVGPFKS-CGLYQLBNSA-N

Purity

>98%

Density

1.421 g/cm3

Appearance

Powder

Application

Anti-estrogenic

Form

Powder