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SMB00091

Sigma-Aldrich

Altholactone

≥95% (LC/MS-ELSD)

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About This Item

Formule empirique (notation de Hill):
C13H12O4
Numéro CAS:
65408-91-5
Poids moléculaire :
232.23
Numéro MDL:
MFCD23103612
Code UNSPSC :
12352205
ID de substance PubChem :
329824769
Nomenclature NACRES :
NA.25

Pureté

≥95% (LC/MS-ELSD)

Forme

solid

Application(s)

metabolomics
vitamins, nutraceuticals, and natural products

Température de stockage

−20°C

Chaîne SMILES 

O[C@H]1[C@@H]2OC(=O)C=C[C@@H]2O[C@@H]1c3ccccc3

InChI

1S/C13H12O4/c14-10-7-6-9-13(17-10)11(15)12(16-9)8-4-2-1-3-5-8/h1-7,9,11-13,15H/t9-,11+,12+,13+/m0/s1

Clé InChI

ZKIRVBNLJKGIEM-WKSBVSIWSA-N

Description générale

Natural product derived from plant source.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301

Conseils de prudence

P301 + P310

Classification des risques

Acute Tox. 3 Oral

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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William P Unsworth et al.
Chemical communications (Cambridge, England), 47(27), 7659-7661 (2011-06-15)
We describe a concise synthesis of (+)-isoaltholactone via a Au-catalysed cyclisation of a monoallylic diol to form the tetrahydrofuranyl ring. Analogous cyclisations show that the stereochemical outcome is dictated by the stereochemistry of the diol substrate.
Shuchi Gupta et al.
Bioorganic & medicinal chemistry, 18(2), 849-854 (2009-12-29)
A related series of styryllactones with small functional and stereochemical variations were compiled for a comparative study of their apoptotic activities toward two tumorigenic and one non-tumorigenic control cell line. While a substantial range of intrinsic activity was observed, the
Nizar M Mhaidat et al.
Phytotherapy research : PTR, 26(6), 926-931 (2011-11-23)
Resistance of colorectal cancer (CRC) to the available chemotherapy reveals the demand for identification of new anticancer agents. We evaluated the antitumour potential of altholactone, a naturally occurring bioactive compound isolated from Goniothalamus spp. (Annonaceae) hooks, against CRC cells. Antitumour
Kavirayani R Prasad et al.
The Journal of organic chemistry, 73(1), 2-11 (2007-05-26)
Stereoselective total synthesis of biologically active styryllactones 7-epi-goniofufurone, goniofufurone, goniopypyrone, goniotriol, altholactone, and etharvensin was achieved in high overall yields from a common intermediate derived from d-(-)-tartaric acid. It is based on the utility of a masked tetrol, comprising an
Dieter Enders et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 14(9), 2842-2849 (2008-01-26)
The asymmetric total synthesis of (+)-altholactone (1), a member of the styryllactone family of natural products displaying cytotoxic and antitumor activities, is described. Key steps include a RAMP-hydrazone alpha-alkylation (RAMP=(R)-1-amino-2-methoxymethylpyrrolidine) of 2,2-dimethyl-1,3-dioxan-5-one, a boron-mediated aldol reaction, a six- to five-membered
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