SMB00091
Altholactone
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About This Item
Empirical Formula (Hill Notation):
C13H12O4
CAS Number:
Molecular Weight:
232.23
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352205
MDL number:
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
SMILES string
O[C@H]1[C@@H]2OC(=O)C=C[C@@H]2O[C@@H]1c3ccccc3
InChI key
ZKIRVBNLJKGIEM-WKSBVSIWSA-N
form
solid
application(s)
metabolomics
vitamins, nutraceuticals, and natural products
Related Categories
General description
Natural product derived from plant source.
signalword
Danger
hcodes
pcodes
Hazard Classifications
Acute Tox. 3 Oral
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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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
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
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.
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