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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.)

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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
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
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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