| Identification | Back Directory | [Name]
annonacin | [CAS]
111035-65-5 | [Synonyms]
annonacin
(+/-) Annonacin (Mixture of Isomers)
(5S)-5-Methyl-3-[(2R,8R,13R)-2,8,13-trihydroxy-13-[[(2R)-tetrahydro-5α-[(R)-1-hydroxytridecyl]furan]-2β-yl]tridecyl]-2(5H)-furanone
2(5H)-Furanone, 5-methyl-3-[(2R,8R,13R)-2,8,13-trihydroxy-13-[(2R,5R)-tetrahydro-5-[(1R)-1-hydroxytridecyl]-2-furanyl]tridecyl]-, (5S)- | [Molecular Formula]
C35H64O7 | [MDL Number]
MFCD27664980 | [MOL File]
111035-65-5.mol | [Molecular Weight]
596.88 |
| Chemical Properties | Back Directory | [Melting point ]
69-71 °C | [Boiling point ]
756.2±55.0 °C(Predicted) | [density ]
1.050±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMF: 10 mg/ml; DMSO: 20 mg/ml; DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml; Ethanol: 1 mg/ml | [form ]
A powder | [pka]
14.45±0.20(Predicted) | [color ]
White to off-white | [InChIKey]
XNODZYPOIPVPRF-CGWDHHCXSA-N | [SMILES]
O1[C@@H](C)C=C(C[C@H](O)CCCCC[C@@H](O)CCCC[C@@H](O)[C@H]2CC[C@H]([C@H](O)CCCCCCCCCCCC)O2)C1=O |
| Hazard Information | Back Directory | [Uses]
(+/-) Annonacin is used as a modulation of cancer signaling pathway(s) in two -stage mouse skin tumorigenesis by annonacin. Its also used in the evaluation of nutritional characteristics and bioactive compounds of Annona muricata-yogurt and Annona muricata-frozen dessert. | [in vivo]
Annonacin (0-9 mg/kg; Subcutaneous osmotic pump; 3 days) increases tau phosphorylation in R406W+/+ mice [3].
Annonacin (85 nM/100 μL; Topical application; Twice a week for 22 weeks) has anti-cancer effect in mouse model of skin tumor [4]. | Animal Model: | R406W+/+ transgenic mice[3] | | Dosage: | 0, 6 and 9 mg/kg/day | | Administration: | Subcutaneous osmotic pump; 3 days | | Result: | Increased the number of neurons with phosphorylated tau in the somatodendritic compartment in several brain areas.
Increased the levels of phosphorylated tau protein.
Increased in total tau protein without increase in tau mRNA, but reduced proteasomal proteolytic activity.
Increased the levels of different tau kinases.
Significantly increased the ratio of p25/p35.
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| Animal Model: | DMBA (HY-W011845)/TPA treated female ICR mice aged 6-7 weeks old[4] | | Dosage: | 85 nM/100 uL | | Administration: | Topical application; Twice a week for 22 weeks | | Result: | Significantly increased the tumor latency period and reduced the tumor incidence, tumor burden and tumor volume, respectively.
Suppressed tumorigenesis manifested by significant reduction of hyperkeratosis, dermal papillae and number of keratin pearls on skin tissues.
Showed no toxicity to the liver and kidneys.
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| [storage]
Store at -20°C |
|
| Company Name: |
BioBioPha Co., Ltd. Gold
|
| Tel: |
0871-65217109 13211707573; |
| Website: |
http://www.biobiopha.com |
|