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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

Quality Level

100

assay

98%

form

solid

optical activity

[α]20/D +133°, c = 4 in ethanol

mp

193-196 °C (lit.)

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)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Yong-Mei Cui et al.
Bioorganic & medicinal chemistry letters, 18(19), 5197-5200 (2008-09-16)
We found that the podocarpic acid structure provides a new scaffold for chemical modulators of large-conductance calcium-activated K(+) channels (BK channels). Structure-activity analysis indicates the importance of both the arrangement (i.e., location and orientation) of the carboxylic acid functionality of
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
E J Parish et al.
Journal of pharmaceutical sciences, 73(5), 694-696 (1984-05-01)
As a class, octahydrophenanthrene lactones, podolactones , and related podocarpic acid derivatives have been reported to possess a wide variety of biological activities, including antileukemic activity, inhibition of plant cell growth, and hormonal and anti-inflammatory properties. In the present study
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
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