559-74-0
Friedelin
CAS: 559-74-0
Molecular Formula: C30H50O
559-74-0 - Names and Identifiers
| Name | Friedelin |
| Synonyms | Friedelin FRIEDELIN NSC 55141 Friedeline FRIEDELIN hplc Friedelan-3-one FRIEDELAN-3-ONE FRIEDELIN, TECH. FRIEDELIN WITH HPLC DA-FRIEDOOLEANAN-3-ONE DA-friedooleanan-3-one, Friedelan-3-one 4,4a,6b,8a,11,11,12b,14a-octamethylicosahydropicen-3(2H)-one (4R,4aS,6bR,8aR,12bS,14aS)-4,4a,6b,8a,11,11,12b,14a-octamethylicosahydropicen-3(2H)-one (4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS)-4,4a,6b,8a,11,11,12b,14a-octamethylicosahydropicen-3(2H)-one |
| CAS | 559-74-0 |
| EINECS | 209-205-1 |
| InChI | InChI=1/C30H50O/c1-20-21(31)9-10-22-27(20,5)12-11-23-28(22,6)16-18-30(8)24-19-25(2,3)13-14-26(24,4)15-17-29(23,30)7/h20,22-24H,9-19H2,1-8H3/t20-,22?,23?,24?,26+,27+,28-,29+,30-/m0/s1 |
559-74-0 - Physico-chemical Properties
| Molecular Formula | C30H50O |
| Molar Mass | 426.72 |
| Density | 0.963±0.06 g/cm3(Predicted) |
| Melting Point | 262-265 °C (lit.) |
| Boling Point | 477.2±13.0 °C(Predicted) |
| Specific Rotation(α) | D -27.8° (chloroform) |
| Flash Point | 233.9°C |
| Solubility | Soluble in chloroform, petroleum ether and other organic solvents, insoluble in water. |
| Vapor Presure | 2.86E-09mmHg at 25°C |
| Appearance | White needle crystal |
| Color | White to Off-White |
| Merck | 13,4293 |
| BRN | 1916451 |
| Storage Condition | 2-8°C |
| Refractive Index | 1.502 |
| MDL | MFCD00017296 |
559-74-0 - Risk and Safety
| WGK Germany | 3 |
559-74-0 - Reference
| Reference Show more | 1. [IF=5.89] Gao Hai-Yun et al."Metabolic Engineering of Saccharomyces cerevisiae for High-Level Friedelin via Genetic Manipulation."Front Bioeng Biotech. 2022 Feb;0:99 |
559-74-0 - Reference Information
| properties | unrestrained terpene (Friedelin) is a typical triterpenoid, belonging to the type of pentacyclic triterpene, white needle-like crystals, melting point 263-263.5 ℃, soluble in chloroform, petroleum ether and other organic solvents, insoluble in water. |
| form of existence | Cork ketone exists in many plants, such as the whole grass of Euphorbiaceae, plants of the family stauridae, such as The dendrimer of litmus basmus. |
| Application | Cork ketone has a wide range of biological activity and medical applications, such as anti-inflammatory, analgesic, antioxidant, free radical scavenging and good inhibition of pathogenic bacteria and fungi. It also has insecticidal effect and can be applied to plant protection. |
| preparation | raw material, take 1kg, add 5 times the amount of n-hexane, heat reflux extraction 4 times, 2h each time, the extracts were combined, concentrated to extract, washed with 70% ethanol, and then extracted with ethyl acetate. The ethyl acetate extract was concentrated to a small volume, added with appropriate amount of silica gel, stirred evenly, dry on silica gel column, followed by 8: 1, 19: 1, 24: 1, 47: 1 chloroform-methanol mixed solution was eluted, the eluate rich in uninhibited terpene components was collected, and the eluate was dissolved by ethanol reflux, and cooled to crystallize, this was repeated twice, and the crystals were filtered off and dried to obtain 3.1g of the Cork ketone product, with a content of 92.7%. |
| biological activity | Friedelin was isolated from leaves of Maytenus ilifolia (Mart). Friedelin is a non-competitive inhibitor of CYP3A4 with IC50 and Ki values of 10.79 μm and 6.16 μm, respectively. Friedelin is also a competitive inhibitor of CYP2E1 with IC50 and Ki values of 22.54 μm and 18.02 μm, respectively. |
| Target | IC50: 10.79 μm (CYP3A4), 22.54 μm (CYP2E1); Ki: 6.16 μm (CYP3A4), 18.02 μm (CYP2E1) |
Last Update：2024-04-09 20:48:19
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