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SMB00091

Sigma-Aldrich

Altholactone

≥95% (LC/MS-ELSD)

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About This Item

Empirical Formula (Hill Notation):
C13H12O4
CAS Number:
65408-91-5
Molecular Weight:
232.23
MDL number:
MFCD23103612
UNSPSC Code:
12352205
PubChem Substance ID:
329824769
NACRES:
NA.25

assay

≥95% (LC/MS-ELSD)

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

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

InChI key

ZKIRVBNLJKGIEM-WKSBVSIWSA-N

Related Categories

General description

Natural product derived from plant source.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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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
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
Barry M Trost et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 13(34), 9547-9560 (2007-09-12)
The use of a mixture of dl- and meso-divinylethylene carbonate as an electrophile in palladium-catalyzed asymmetric allylic alkylation reactions is reported. From the diastereomeric mixture of meso and chiral racemic starting materials, a single product is obtained in high optical
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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