1,4-alpha-Dimethyl-6-hydroxy-1,2,3,4-alpha-9,10,10-alpha-octahydro-1-phenanthrenecarboxylicacid

Name	Podocarpic acid
Synonyms	Podocarpic acid (1S)-1,2,3,4,4aβ,9,10,10aα-Octahydro-6-hydroxy-1,4a-dimethyl-1-phenanthrenecarboxylic acid (1R)-1,4aα-Dimethyl-6-hydroxy-1,2,3,4,4a,9,10,10aβ-octahydrophenanthrene-1α-carboxylic 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 1,4-alpha-Dimethyl-6-hydroxy-1,2,3,4-alpha-9,10,10-alpha-octahydro-1-phenanthrenecarboxylicacid (1S,4aS,10aR)-1,2,3,4,4a,9,10,10a-octahydro-6-hydroxy-1,4a-dimethylphenanthrene-1-carboxylic acid 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)
CAS	5947-49-9
EINECS	227-706-3

Molecular Formula	C17H22O3
Molar Mass	274.35
Density	1.182±0.06 g/cm3(Predicted)
Melting Point	193-196 °C (lit.)
Boling Point	449.6±45.0 °C(Predicted)
Specific Rotation(α)	20546 +165° (c = 4 in abs ethanol)
Merck	13,7625
pKa	4.66±0.40(Predicted)
Storage Condition	2-8℃
In vitro study	Podocarpic acid anhydride acts as a 1 nM agonist of LXRalpha and beta receptors. It shows over 8-10-fold better activator of LXR receptors compared to one of the natural ligands, 22-(R)-hydroxy cholesterol, in HEK-293 cells.
In vivo study	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 Ca 2+ flux, which is significantly reduces when the Ca 2+ -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.

WGK Germany

Last Update：2024-01-02 23:10:35

biological activity

Podocarpic acid is a natural product that is an activator of TRPA1 and has a variety of effects.

Last Update：2024-04-09 21:04:16

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CAS: 5947-49-9
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1,4-alpha-Dimethyl-6-hydroxy-1,2,3,4-alpha-9,10,10-alpha-octahydro-1-phenanthrenecarboxylicacid Request for Quotation