Resinone
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| Category | Others |
| Catalog number | BBF-05389 |
| CAS | 43043-12-5 |
| Molecular Weight | 440.70 |
| Molecular Formula | C30H48O2 |
| Purity | >98% |
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Description
Resinone is a bioactive chemical.
Specification
| Synonyms | Lup-20(29)-en-3-one, 16-hydroxy-, (16β)-; 16-Hydroxylup-20(29)-en-3-one; Lup-20(29)-en-3-one, 16-hydroxy-, (16beta)-; (1R,3aS,4S,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-4-hydroxy-3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)icosahydro-9H-cyclopenta[a]chrysen-9-one; 16β-Hydroxylup-20(29)-en-3-one |
| Storage | Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years) |
| IUPAC Name | (1R,3aS,4S,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-4-hydroxy-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1H-cyclopenta[a]chrysen-9-one |
| Canonical SMILES | CC(=C)C1CCC2(C1C3CCC4C5(CCC(=O)C(C5CCC4(C3(CC2O)C)C)(C)C)C)C |
| InChI | InChI=1S/C30H48O2/c1-18(2)19-11-14-28(6)24(32)17-30(8)20(25(19)28)9-10-22-27(5)15-13-23(31)26(3,4)21(27)12-16-29(22,30)7/h19-22,24-25,32H,1,9-17H2,2-8H3/t19-,20+,21-,22+,24-,25+,27-,28+,29+,30+/m0/s1 |
| InChI Key | SOKRNBGSNZXYIO-GEWJJWOZSA-N |
Properties
| Appearance | Solid Powder |
| Boiling Point | 516.0±50.0°C at 760 mmHg |
| Density | 1.0±0.1 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1. [Chemical constituents from the aerial part of Stauntonia obovatifoliola Hayata subsp. urophylla]
Xiao-bing Peng, Wei-lue Gao, Dong-qun Hu, Fang-fang Ma, Li-gang Fu, Qian Deng, Ying Wei Zhong Yao Cai. 2013 Nov;36(11):1795-8.
Objective: To study the chemical constituents of the aerial part of Stauntonia obovatifoliola. Methods: The chemical constituents of ethyl acetate fraction were isolated and purified by several chromatography. Their structures were elucidated by their physiochemical properties and spectral methods. Results: Six known compounds were isolated and identified as lupeone(1), lupeol(2), stigmasterol(3),3beta-O-acetyloleanolic acid(4), resinone(5) and daucosterol(6). Conclusion: Compounds 1-6 are isolated from this plant for the first time.
2. The influence of friedelin, resinone, tingenone and betulin of compounds on chondrogenic differentiation of porcine adipose-derived mesenchymal stem cells (pADMSCs)
Mapula Razwinani, Keolebogile Shirley Motaung Biochimie. 2022 May;196:234-242. doi: 10.1016/j.biochi.2022.01.018. Epub 2022 Feb 2.
The study investigated the influence of friedelin, resinone, tingenone and betulin plant-based secondary metabolite compounds on cellular proliferation, extracellular matrix (ECM) components synthesis, expression of chondrogenic markers and maturation of differentiated chondrocytes (cell proliferation and hypertrophy) in porcine adipose-derived mesenchymal stem cells (pADMSCs) undergoing chondrogenic differentiation. The MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) and Cyquant assays were used to determine cell proliferation, viability, and total cellular DNA, DMMB (Dimethyl methylene blue) was used for glycosaminoglycan (GAG) synthesis, RT-qPCR for gene expression and histology combined with immunohistochemistry for cartilage ECM proteoglycan deposition. The MTT results showed that friedelin at 37 μM, resinone at 36 μM and betulin at 18 μM with cell viability of above 100% compared to control. Tingenone at 37 μM showed cell viability of about 76%. These concentrations were considered the most effective with no toxicity effect on the cells and were further analysed with TGF-β3 (10 ng/mL) as a positive control. The results showed a high synthesis of DNA with friedelin on day 14. There was up-regulation of SOX 9, Col II and Col X with friedelin and resinone at day 14 with the significance of p < 0.01. Pellet from friedelin, resinone and tingenone showed more staining of the matrix for Safranin-O and Toluidine blue at day 14. Immunohistostaining of collagen type X (COL-10) showed more stain intensity at friedelin and resinone on day 21. These results provided new knowledge on the potential use of natural isolated secondary metabolites compounds as inducers for chondrogenic and bone differentiation.
3. [Chemical constituents from bark of Caragana opulens]
Zhong-Duo Yang, An-Rong Xiao, Xu Zhang, Tao Li, Shuo Li Zhong Yao Cai. 2008 Jun;31(6):855-7.
Objective: To investigate the chemical constituents of the bark of Caragana opulens. Methods: The constituents of the CH3Cl-soluble portion in the 95% ethanol extract were isolated and purified by means of chromatography. The compounds were identified by their physical characteristics and spectral features. Results: Eight compounds were isolated and identified as encelin(1), (+)-13-Hydroxyspathulenol(2), (+) -3alpha,9beta-aromaden dranediol(3), quercetin(4), penduletin(5), lupenol(6), Lup-20(29) -en-3-one (7), beta-sitosterol(8). Conclusion: Compounds 1, 2, 5, 7 are isolated for the first time from Caragana genus.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
