Basic information Safety Supplier Related

PODOCARPIC ACID

Basic information Safety Supplier Related

PODOCARPIC ACID Basic information

Product Name:
PODOCARPIC ACID
Synonyms:
  • (1S,4aS,10aR)-1,2,3,4,4a,9,10,10a-octahydro-6-hydroxy-1,4a-dimethylphenanthrene-1-carboxylic acid
  • 1,4-alpha-Dimethyl-6-hydroxy-1,2,3,4-alpha-9,10,10-alpha-octahydro-1-phenanthrenecarboxylicacid
  • 1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-6-hydroxy-1,4a-dimethyl-, (1S,4aS,10aR)-
  • 1-Phenanthrenecarboxylic acid, 1,2,3,4,4a,9,10,10a-octahydro-6-hydroxy -1,4a-dimethyl-, (1S-(1alpha,4aalpha,10abeta))- (9CI)
  • (1S)-1,2,3,4,4aβ,9,10,10aα-Octahydro-6-hydroxy-1,4a-dimethyl-1-phenanthrenecarboxylic acid
  • (1S)-1,4aβ-Dimethyl-6-hydroxy-1,2,3,4,4a,9,10,10aα-octahydrophenanthrene-1β-carboxylic acid
  • [1S,(+)]-1,2,3,4,4a,9,10,10aα-Octahydro-6-hydroxy-1,4aβ-dimethyl-1β-phenanthrenecarboxylic acid
  • (1R)-1,4aα-Dimethyl-6-hydroxy-1,2,3,4,4a,9,10,10aβ-octahydrophenanthrene-1α-carboxylic acid
CAS:
5947-49-9
MF:
C17H22O3
MW:
274.35
EINECS:
227-706-3
Product Categories:
  • Asymmetric Synthesis
  • Chiral Building Blocks
  • Complex Molecules
Mol File:
5947-49-9.mol
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PODOCARPIC ACID Chemical Properties

Melting point:
193-196 °C (lit.)
alpha 
20546 +165° (c = 4 in abs ethanol)
Boiling point:
449.6±45.0 °C(Predicted)
Density 
1.182±0.06 g/cm3(Predicted)
storage temp. 
Store at -20°C
solubility 
DMSO: ≥ 100 mg/mL (364.50 mM)
pka
4.66±0.40(Predicted)
form 
Solid
color 
White to off-white
optical activity
[α]20/D +133°, c = 4 in ethanol
Merck 
13,7625
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Safety Information

WGK Germany 
3

MSDS

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PODOCARPIC ACID Usage And Synthesis

Uses

Podocarpic acid is a natural product, which has the best all-round positive effect and acts as a novel TRPA1 activator.

Definition

ChEBI: An abietane diterpenoid lacking the isopropyl substituent with an aromatic C-ring and a hydroxy group at the 12-position.

in vivo

Podocarpic acid activates SKN-1 in C. elegans, similar to known Nrf2 activators such as α-lipoic acid (LA). Podocarpic acid- or LA-induced SKN-1 activation also requires TRPodocarpic acid-1: trPodocarpic acid-1 knockdown in glod-4;gst-4p::gfp animals reduces expression of gst-4 to wild-type levels. A and LA supplementation results in a robust Ca2+ flux, which is significantly reduces when the Ca2+-impermeable TRPodocarpic acid-1E1018A channel is present, suggesting that TRPodocarpic acid-1 activation is key for these drugs' function. Finally, Podocarpic acid and LA alleviate the Podocarpic acidthogenic phenotypes of glod-4 animals by reverting the high endogenous MGO and GO to almost wild-type-like levels[1].

References

[1] Baraka HN. Microbial transformation of podocarpic acid and evaluation of transformation products for antioxidant activity. Planta Med. 2010 May;76(8):815-7. DOI:10.1055/s-0029-1240738
[2] Singh S, et al. Discovery and development of dimeric podocarpic acid leads as potent agonists of liver X receptor with HDL cholesterol raising activity in mice and hamsters. Bioorg Med Chem Lett. 2005 Jun 2;15(11):2824-8. DOI:10.1016/j.bmcl.2005.03.100

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