| Identification | Back Directory | [Name]
PODOCARPIC ACID | [CAS]
5947-49-9 | [Synonyms]
Nsc 231784
PODOCARPIC ACID
Einecs 227-706-3
Podocarpic acid 98%
Podocarpic acid, >99%
12-HYDROXYPODOCARPA-8,11,13-TRIEN-16-OIC ACID
Podocarpa-8,11,13-trien-16-oic acid, 12-hydroxy- (van) (8ci)
1 4A-DIMETHYL-6-HYDROXY-1 2 3,4A 9 10 10A-OCTAHYDRO-1-PHENANTHRENECARBOXYLIC ACID
1,2,3,4,4a,9,10,10aβ-Octahydro-6-hydroxy-1,4aα-dimethyl-1α-phenanthrenecarboxylic acid
(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
(1R)-1,4aα-Dimethyl-6-hydroxy-1,2,3,4,4a,9,10,10aβ-octahydrophenanthrene-1α-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) | [EINECS(EC#)]
227-706-3 | [Molecular Formula]
C17H22O3 | [MDL Number]
MFCD00074825 | [MOL File]
5947-49-9.mol | [Molecular Weight]
274.35 |
| Chemical Properties | Back Directory | [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) | [form ]
Solid | [pka]
4.66±0.40(Predicted) | [color ]
White to off-white | [Optical Rotation]
[α]20/D +133°, c = 4 in ethanol | [Merck ]
13,7625 | [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 | [InChIKey]
VJILEYKNALCDDV-OIISXLGYSA-N | [SMILES]
[H][C@@]12CCc3ccc(O)cc3[C@@]1(C)CCC[C@]2(C)C(O)=O |
| Hazard Information | Back Directory | [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]. | [storage]
Store at -20°C | [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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