| Identification | Back Directory | [Name]
FRIEDELIN | [CAS]
559-74-0 | [Synonyms]
FRIEDELIN
Nsc 55141
Friedeline
3-Friedelanone
FRIEDELIN hplc
FRIEDELAN-3-ONE
FRIEDELIN, TECH.
Einecs 209-205-1
FRIEDELIN WITH HPLC
DA-FRIEDOOLEANAN-3-ONE
Friedelin technical grade
DA-friedooleanan-3-one, Friedelan-3-one
D:A-Friedooleanan-3-one (van) (8ci)(9ci)
Friedelin,DA-friedooleanan-3-one, Friedelan-3-one
(4β,5β,8α,9β,10α,13α,14β)-5,9,13-Trimethyl-24,25,26-trinoroleanan-3-one
24,25,26-Trinoroleanan-3-one, 5,9,13-trimethyl-, (4β,5β,8α,9β,10α,13α,14β)-
(4R,4aS,6aS,6aS,6bR,8aR,12aR,14aS,14bS)-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1H-picen-3-one | [EINECS(EC#)]
209-205-1 | [Molecular Formula]
C30H50O | [MDL Number]
MFCD00017296 | [MOL File]
559-74-0.mol | [Molecular Weight]
426.72 |
| Chemical Properties | Back Directory | [Melting point ]
262-265 °C(lit.)
| [alpha ]
D -27.8° (chloroform) | [Boiling point ]
477.2±13.0 °C(Predicted) | [density ]
0.963±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
neat | [color ]
White to Off-White | [Optical Rotation]
-2214 (c 0.8, CHCl3) | [Merck ]
13,4293 | [BRN ]
1916451 | [Major Application]
food and beverages | [InChIKey]
OFMXGFHWLZPCFL-SVRPQWSVSA-N | [SMILES]
C[C@H]1C(=O)CC[C@@H]2[C@]1(C)CC[C@H]3[C@@]2(C)CC[C@@]4(C)[C@@H]5CC(C)(C)CC[C@]5(C)CC[C@]34C | [LogP]
10.287 (est) |
| Hazard Information | Back Directory | [Uses]
Friedelin can be used as a starting material in the synthesis of:
- Friedel-3-enol acetate, friedel-2-oxo-3-enol acetate, friedel-2-ene derivatives and friedelin ketoxime.
- Oxygenated friedelin derivatives as potent DNA topoisomerase IIα inhibitors.
- Its 1,4-pyrazine derivatives as potent antimicrobial agents.
| [Uses]
Friedelin is a flavonoid extract which displays radical scavenging and anti-typhoid activity. | [Definition]
ChEBI: Friedelin is a pentacyclic triterpenoid that is perhydropicene which is substituted by an oxo group at position 3 and by methyl groups at the 4, 4a, 6b, 8a, 11, 11, 12b, and 14a-positions (the 4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS-enantiomer). It is the major triterpenoid constituent of cork. It has a role as an anti-inflammatory drug, a non-narcotic analgesic, an antipyretic and a plant metabolite. It is a pentacyclic triterpenoid and a cyclic terpene ketone. | [General Description]
Friedelin, a pentacyclic triterpene, is found in several plants like Cissus quadrangularis, Celastrus vulcanicola, Terminalia?avicennioides, and Alangium salvifolium. It is known to act as a histamine H1 receptor?(H1R) antagonist, anti-microbial, anti-HIV, and anti-cancer agent. | [Synthesis]
Crude bamboo powder as raw materials, take 1kg, add 5 times the amount of n-hexane, heating and reflux extraction 4 times, each time 2h, combined extract, concentrated to extract, washed with 70% ethanol, and then extracted with ethyl acetate, ethyl ac | [in vivo]
Friedelin (40 mg/kg, p.o., single dose) exhibits potent anti-inflammatory activity in the carrageenan (HY-125474)-induced acute inflammation Wistar rat model[2].
Friedelin (30 mg/kg, i.p., once daily, for 14 days) alleviats neuronal dysfunction and memory impairment in the scopolamine (HY-N0296)-induced neurodegeneration mouse model[3].
Friedelin (40 μM, local injection near the right Achilles tendon, once weekly, for 4 weeks) prevents the progression of tendinopathy in the type I collagenase (HY-E70005A)-induced tendinopathy C57BL/6 mouse model[4]. | Animal Model: | Scopolamine (HY-N0296)-induced neurodegeneration mice model[3] | | Dosage: | 30 mg/kg | | Administration: | Intraperitoneal injection (i.p.), once daily, for 14 days | | Result: | Improved scopolamine-induced oxidative stress, neurodegeneration, and memory impairment. |
| Animal Model: | Carrageenan (HY-125474)-induced acute inflammation Wistar rats model[2] | | Dosage: | 40 mg/kg | | Administration: | Oral gavage (p.o.), single dose | | Result: | Maximally inhibited acute inflammatory response, significantly reduced paw edema thickness. |
| Animal Model: | Collagenase Type I (HY-E70005A)-induced tendinopathy C57BL/6 mice model[4] | | Dosage: | 40 μM | | Administration: | Local injection near the right Achilles tendon, once weekly, for 4 weeks | | Result: | Significantly improved tendon mechanical strength, reduced inflammatory cell infiltration, restored ordered collagen fiber arrangement. |
| [IC 50]
CYP2; CYP3 |
|
|