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119792

Sigma-Aldrich

Podocarpic acid

98%

Synonym(s):

(+)-Podocarpic acid, (1S)-1,2,3,4,4a,9,10,10a-Octahydro-6-hydroxy-1,4a-dimethyl-1-phenanthrenecarboxylic acid, (1S,4aS,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-6-hydroxy-1,4a-dimethyl-1-phenanthrenecarboxylic acid, Podocarpic acid (resin acid)

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About This Item

Empirical Formula (Hill Notation):
C17H22O3
CAS Number:
5947-49-9
Molecular Weight:
274.35
EC Number:
227-706-3
MDL number:
MFCD00074825
UNSPSC Code:
12352002
PubChem Substance ID:
24847299
NACRES:
NA.22

assay

98%

form

solid

optical activity

[α]20/D +133°, c = 4 in ethanol

mp

193-196 °C (lit.)

functional group

carboxylic acid

SMILES string

[H][C@@]12CCc3ccc(O)cc3[C@@]1(C)CCC[C@]2(C)C(O)=O

InChI

1S/C17H22O3/c1-16-8-3-9-17(2,15(19)20)14(16)7-5-11-4-6-12(18)10-13(11)16/h4,6,10,14,18H,3,5,7-9H2,1-2H3,(H,19,20)/t14-,16-,17+/m1/s1

InChI key

VJILEYKNALCDDV-OIISXLGYSA-N

Gene Information

human ... TNF(7124)

Related Categories

Application

  • (+)-Podocarpic acid as chiral template in the synthesis of aphidicolane, stemodane and stemarane diterpenoids: This article reviews the use of (+)-podocarpic acid in the synthesis of various diterpenoids, showcasing its utility in complex organic syntheses (La Bella et al., 2016).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW0967
MKCW9400
MKCV9924
MKCV1320
MKCT1910

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K A Staschke et al.
Virology, 248(2), 264-274 (1998-08-29)
Entry of influenza virus into the host cell is dependent on the fusion of the viral envelope with the endosomal membrane and is mediated by a low-pH-induced change of the viral hemagglutinin (HA) to a conformation that is fusogenic. A
Weiguo Liu et al.
Bioorganic & medicinal chemistry letters, 15(20), 4574-4578 (2005-08-30)
A series of podocarpic acid amides were identified as potent agonists for Liver X receptor alpha and beta subtypes, which are members of a nuclear hormone receptor superfamily that are involved in the regulation of a variety of metabolic pathways
A E Fidler et al.
Reproduction, fertility, and development, 12(3-4), 191-199 (2001-04-17)
In recent years the possibility of environmental oestrogens affecting the reproduction of vertebrates has become an issue of both public and scientific interest. Although the significance of such chemicals remains controversial there is clear evidence that, in some contexts, environmental
Podocarpic acid as a source of an oestrogenic hormone.
C W BRANDT et al.
Nature, 161(4101), 892-892 (1948-06-05)
D J Bennett et al.
Current medicinal chemistry, 15(2), 195-209 (2008-01-29)
The Liver X Receptor (LXR) alpha and beta isoforms are members of the type II nuclear receptor family which function as a heterodimer with the Retinoid X Receptor (RXR). Upon agonist binding, the formation of the LXR/RXR heterodimer takes place
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