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19533-92-7

19533-92-7 structure
19533-92-7 structure
  • Name: (2α,3β)-2,3-Dihydroxylup-20(29)-en-28-oic acid
  • Chemical Name: 2α,3β-dihydroxy-20(29)-lupen-28-oic acid
  • CAS Number: 19533-92-7
  • Molecular Formula: C30H48O4
  • Molecular Weight: 472.700
  • Catalog: Natural product Moss
  • Create Date: 2016-02-06 12:38:22
  • Modify Date: 2025-08-21 14:40:59
  • Alphitolic acid (Aophitolic acid) is an anti-inflammatory triterpene could found in quercus aliena. Alphitolic acid blocks Akt–NF-κB signaling to induce apoptosis. Alphitolic acid induces autophagy. Alphitolic acid has anti-inflammatory activity and down-regulates the NO and TNF-α production. Alphitolic acid can be used for cancer and inflammation research[1][2][3].
Name 2α,3β-dihydroxy-20(29)-lupen-28-oic acid
Synonyms Lup-20(29)-en-28-oic acid, 2,3-dihydroxy-, (2α,3β)-
2alpha,3beta-dihydroxy-20(29)-lupen-28-oic acid
Alphitolic acid
(2α,3β)-2,3-Dihydroxylup-20(29)-en-28-oic acid
Description Alphitolic acid (Aophitolic acid) is an anti-inflammatory triterpene could found in quercus aliena. Alphitolic acid blocks Akt–NF-κB signaling to induce apoptosis. Alphitolic acid induces autophagy. Alphitolic acid has anti-inflammatory activity and down-regulates the NO and TNF-α production. Alphitolic acid can be used for cancer and inflammation research[1][2][3].
Related Catalog
In Vitro Alphitolic acid (Aophitolic acid) (0-30 µM; 72 hours; HSC-3, SCC2095, and SCC4 cells) has anti-proliferative activity in oral cancer cells in a dose-dependent manner, induces apoptosis and blocks Akt–NF-κB signaling[1]. Alphitolic acid (Aophitolic acid) (0-25 µM; 3-72 hours; SCC4 cells) induces autophagy with increases the expression of autophagosome marker LC3B-II and two autophagyregulatory proteins[1]. Alphitolic acid (Aophitolic acid) (0-25 µM; 72 hours; SCC4 cells) increases p53 phosphorylation and expression, decreases in the expression of the oncogenic E3 ligase MDM2[1]. Alphitolic acid (Aophitolic acid) (0-25 µM; 72 hours; RAW 264.7 macrophages) has anti-inflammatory activity and down-regulates the NO and TNF-α production with IC50 values of 17.6 and 22.7 µM, respectively[2]. Cell Viability Assay[1] Cell Line: HSC-3, SCC2095 and SCC4 cells Concentration: 0, 10, 15, 20, 25 and 30 µM Incubation Time: 72 hours Result: Suppressed the proliferation of SCC4 and SCC2095 cells with IC50 values of 12 and 15 µM, respectively. Apoptosis Analysis[1] Cell Line: SCC4 cells Concentration: 0, 10, 20 and 30 µM Incubation Time: 72 hours Result: Increased the percentage of apoptotic cells from 11.8% to 25.1% in a dose-dependent manner. Western Blot Analysis[1] Cell Line: SCC4 cells Concentration: 0, 10, 15 and 20 µM Incubation Time: 72 hours Result: Decreased the expression of phosphorylation of Akt and its downstream substrates, including p70S6K, S6, and IκBα. Down-regulated the expression of NF-κB and its downstream target gene product Bcl-2. Western Blot Analysis[1] Cell Line: SCC4 cells Concentration: 0, 10, 15, 20 and 25 µM Incubation Time: 3, 6, 12, 24, 48 and 72 hours Result: Increased autophagosome marker LC3B-II in a dose- and time-dependent manner. Increased the expression of autophagy-related protein 7 (Atg7).
In Vivo Alphitolic acid (Aophitolic acid) (47-756 µg/ear; i.h.; adult male CF-1 mice) has anti-inflammatory activity in vivo[3]. Animal Model: Adult male CF-1 mice[3] Dosage: 47, 94, 330, 378 and 756 µg/ear Administration: subcutaneous injection Result: Had anti-inflammatory activity with an ED50 of 0.11 and 0.20 µM in a dose-dependent.
References

[1]. Bai LY, et, al. Alphitolic acid, an anti-inflammatory triterpene, induces apoptosis and autophagy in oral squamous cell carcinoma cells, in part, through a p53-dependent pathway. 2015 Jan 22; 18(2015):368-378.

[2]. Raju R, et, al. Anti-Inflammatory Chemical Profiling of the Australian Rainforest Tree Alphitonia petriei (Rhamnaceae). Molecules. 2016 Nov 11;21(11):1521.

[3]. Goity LE, et, al. An HPLC-UV and HPLC-ESI-MS based method for identification of antiinflammatory triterpenoids from the extracts of Ugni molinae. 2013 Jan; 12(1):108-116.
Density 1.1±0.1 g/cm3
Boiling Point 566.4±30.0 °C at 760 mmHg
Molecular Formula C30H48O4
Molecular Weight 472.700
Flash Point 310.4±21.1 °C
Exact Mass 472.355255
PSA 77.76000
LogP 7.76
Vapour Pressure 0.0±3.5 mmHg at 25°C
Index of Refraction 1.546
Hazard Codes Xi
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