Tessaric acidCAS# 58142-10-2 |
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| Cas No. | 58142-10-2 | SDF | Download SDF |
| PubChem ID | 14527134 | Appearance | Powder |
| Formula | C15H20O3 | M.Wt | 248.3 |
| Type of Compound | Sesquiterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | 2-[(2R,8S,8aR)-8,8a-dimethyl-6-oxo-1,2,3,4,7,8-hexahydronaphthalen-2-yl]prop-2-enoic acid | ||
| SMILES | CC1CC(=O)C=C2C1(CC(CC2)C(=C)C(=O)O)C | ||
| Standard InChIKey | GAWKUNMREBFQOL-ZVWUFJHRSA-N | ||
| Standard InChI | InChI=1S/C15H20O3/c1-9-6-13(16)7-12-5-4-11(8-15(9,12)3)10(2)14(17)18/h7,9,11H,2,4-6,8H2,1,3H3,(H,17,18)/t9-,11+,15+/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Tessaric acid has antifeedant and allelochemical effects. Tessaric acid derivatives induce G/M cell cycle arrest in human solid tumor cell lines. |
| In vitro | Tessaric acid derivatives induce G2/M cell cycle arrest in human solid tumor cell lines.[Pubmed: 19664930 ]Bioorg Med Chem. 2009 Sep 1;17(17):6251-6.
Antifeedant/insecticidal terpenes from asteraceae and labiatae species native to Argentinean semi-arid lands.[Pubmed: 16402545 ]Z Naturforsch C. 2005 Nov-Dec;60(11-12):855-61.To validate the potential as added-value resources of Asteraceae and Labiatae species of Argentinean semi-arid lands, we have selected 13 of their major terpenoids belonging to several chemical classes and tested their insect antifeedant and toxic activity on the herbivorous insects Spodoptera littoralis and Leptinotarsa decemlineata.
Allelochemical effects of eudesmane and eremophilane sesquiterpenes on Tribolium castaneum larvae.[Pubmed: 12647861]J Chem Ecol. 2003 Jan;29(1):175-87.
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Tessaric acid Dilution Calculator
Tessaric acid Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 4.0274 mL | 20.1369 mL | 40.2739 mL | 80.5477 mL | 100.6847 mL |
| 5 mM | 0.8055 mL | 4.0274 mL | 8.0548 mL | 16.1095 mL | 20.1369 mL |
| 10 mM | 0.4027 mL | 2.0137 mL | 4.0274 mL | 8.0548 mL | 10.0685 mL |
| 50 mM | 0.0805 mL | 0.4027 mL | 0.8055 mL | 1.611 mL | 2.0137 mL |
| 100 mM | 0.0403 mL | 0.2014 mL | 0.4027 mL | 0.8055 mL | 1.0068 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Tessaric acid derivatives induce G2/M cell cycle arrest in human solid tumor cell lines.[Pubmed:19664930]
Bioorg Med Chem. 2009 Sep 1;17(17):6251-6.
A series of analogs were synthesized in a straightforward manner from naturally available sesquiterpenes ilicic acid and Tessaric acid. The in vitro antiproliferative activities were examined in the human solid tumor cell lines A2780, HBL-100, HeLa, SW1573, T-47D and WiDr. The most potent analog induced considerably growth inhibition in the range 1.9-4.5 microM. Cell cycle studies for Tessaric acid derivatives indicated a prominent arrest of the cell cycle at the G(2)/M phase. Damage to the cells was permanent as determine by the so called 24+24 drug schedule.
Antifeedant/insecticidal terpenes from asteraceae and labiatae species native to Argentinean semi-arid lands.[Pubmed:16402545]
Z Naturforsch C J Biosci. 2005 Nov-Dec;60(11-12):855-61.
To validate the potential as added-value resources of Asteraceae and Labiatae species of Argentinean semi-arid lands, we have selected 13 of their major terpenoids belonging to several chemical classes and tested their insect antifeedant and toxic activity on the herbivorous insects Spodoptera littoralis and Leptinotarsa decemlineata. The antifeedant effects of the test compounds were structure- and species-dependent. The most active antifeedant to L. decemlineata was the eudesmane sesquiterpene gamma-costic acid (13), followed by the labdane diterpene 2alpha,3alpha-dihydroxycativic acid (8), the clerodane diterpenes 6-acetylteucjaponin B (5), bacchotricuneatin A (1), bartemidiolide (7), butanolide (4), and the sesquiterpenes ilicic acid (11) and Tessaric acid (10) (eudesmane and eremophilane type, respectively). S. littoralis was only affected by the clerodanes and showed the strongest response to salviarin (3) and 5, followed by hawtriwaic acid (6) and 12-epi-bacchotricuneatin A (2). Orally injected S. littoralis larvae were negatively affected by 5. Most of the diterpenes had selective cytotoxic effects to insect-derived Sf9 cells with the clerodane 1 being the most active, followed by the eudesmane costic acid (12), the only cytotoxic sesquiterpene. None of these compounds was cytotoxic to mammalian CHO cells.
Allelochemical effects of eudesmane and eremophilane sesquiterpenes on Tribolium castaneum larvae.[Pubmed:12647861]
J Chem Ecol. 2003 Jan;29(1):175-87.
Eight eudesmane and eremophilane sesquiterpenes administered to Tribolium castaneum larvae caused different allelochemical effects. Topical application of 3-oxo-gamma-costic acid produced the greatest lengthening in the duration of the pupal stage. Morphological deformities were found, specifically when ilicic, costic, and gamma-costic acids and costic aldehyde were used. Ilicic acid exhibited the major toxicity 72 hr following topical application. All compounds were significantly toxic at the end point of the experiment (60 days). Treated surface toxicity was lower than when topical assays were carried out. Responses to Tessaric acid in choice bioassays had the highest attractive effect. Maximum repellency was caused by the 3-oxo-gamma-costic acid. However, experimental series carried out using gamma-costic acid, eremophilan-1(10),2,11(13)-trien-12-oic acid, costic aldehyde, and ilicic aldehyde showed no clear response.
Enhancement of tessaric acid production in Tessaria absinthioides cell suspension cultures.[Pubmed:30754876]
Plant Cell Rep. 2000 Jul;19(8):821-824.
The total production of the sesquiterpene Tessaric acid (TA) by cell cultures of Tessaria absinthioides at day 25 of the culture period reached 0.086 mg g(-1) DW, with intracellular accumulation accounting for 0.059 mg g(-1) DW. Dimethylsulfoxide-induced permeabilization of the cells effected both total production and extracellular accumulation of the sesquiterpene to reach levels of 148% and 271%, respectively. Cultures treated with elicitor preparations of Verticillum sp., Monodyctis cataneae, Acremonium sp., and Aspergillus niger produced TA at levels of 281%, 197%, 149%, and 139%, respectively. Treatment of cell suspension cultures with cis-(-)-jasmonic acid (5 muM) increased production to 267%, whereas jasmonic acid pretreatment and subsequent elicitation raised external Tessaric acid to 702%.
