alpha-Costic acidCAS# 28399-17-9 |
Quality Control & MSDS
3D structure
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| Cas No. | 28399-17-9 | SDF | Download SDF |
| PubChem ID | 168796 | Appearance | Oil |
| Formula | C15H22O2 | M.Wt | 234.3 |
| Type of Compound | Sesquiterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | 2-[(2R,4aR,8aR)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl]prop-2-enoic acid | ||
| SMILES | CC1=CCCC2(C1CC(CC2)C(=C)C(=O)O)C | ||
| Standard InChIKey | UTXMCYDEIZPGME-VNHYZAJKSA-N | ||
| Standard InChI | InChI=1S/C15H22O2/c1-10-5-4-7-15(3)8-6-12(9-13(10)15)11(2)14(16)17/h5,12-13H,2,4,6-9H2,1,3H3,(H,16,17)/t12-,13+,15-/m1/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. | ||
alpha-Costic acid Dilution Calculator
alpha-Costic acid Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 4.268 mL | 21.3402 mL | 42.6803 mL | 85.3606 mL | 106.7008 mL |
| 5 mM | 0.8536 mL | 4.268 mL | 8.5361 mL | 17.0721 mL | 21.3402 mL |
| 10 mM | 0.4268 mL | 2.134 mL | 4.268 mL | 8.5361 mL | 10.6701 mL |
| 50 mM | 0.0854 mL | 0.4268 mL | 0.8536 mL | 1.7072 mL | 2.134 mL |
| 100 mM | 0.0427 mL | 0.2134 mL | 0.4268 mL | 0.8536 mL | 1.067 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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Inuloxin E, a New Seco-Eudesmanolide Isolated from Dittrichia viscosa, Stimulating Orobanche cumana Seed Germination.[Pubmed:31557920]
Molecules. 2019 Sep 25;24(19). pii: molecules24193479.
A new sesquiterpenoid belonging to the subgroup seco-eudesmanolides and named inuloxin E was isolated from Dittrichia viscosa, together with the already known sesquiterpenoids inuloxins A-D and alpha-Costic acid. Inuloxin E was characterized by spectroscopic data (essentially NMR and ESI MS) as 3-methylene-6-(1-methyl-4-oxo-pentyl)-3a,4,7,7a-tetrahydro-3H-benzofuran-2-one. Its relative configuration was determined by comparison with the closely related inuloxin D and chemical conversion of inuloxin E into inuloxin D and by the observed significant correlation in the NOESY spectrum. Both inuloxins D and E induced germination of the parasitic weed Orobanche cumana, but were inactive on the seeds of Orobanche minor and Phelipanche ramosa. The germination activity of some hemisynthetic esters of inuloxin D was also investigated.
alpha-Costic acid, a plant sesquiterpene with acaricidal activity against Varroa destructor parasitizing the honey bee.[Pubmed:31418584]
Nat Prod Res. 2021 May;35(9):1428-1435.
The organic extract of the aerial parts of Dittrichia viscosa, a perennial native plant of the Mediterranean basin, showed a significant acaricidal activity against Varroa destructor, the parasite mite of Apis mellifera, commonly called honey bee. Among the metabolites isolated from the organic extract of this Asteraceae, alpha-Costic acid showed to be one of the compounds responsible for the toxic activity exhibited by the crude plant extract on this parasite mite species. In addition to the toxic effect a clear acaricidal response has been recorded when the parasitic mite was exposed to 1 mg/mL concentration of alpha-Costic acid while no effects have been showed on honey bees using the same compound at the same concentration. This finding suggests a potential use of alpha-Costic acid to control Varroa mites. The possibility to reliably achieve absolute configuration of alpha-Costic acid by DFT computational analysis of chiroptical spectra has been also demonstrated.(dagger).
Antimould microbial and plant metabolites with potential use in intelligent food packaging.[Pubmed:29027475]
Nat Prod Res. 2018 Jul;32(13):1605-1610.
Moulds food infestation is a heavy dangerous problem for human health and also could generate heavy economic losses. The intelligent packaging using eco-friendly biodegradable biofilm incorporating bioactive natural safe compounds represents a new frontier. This manuscript reports the inhibitory activity of 12 bacterial, fungal and plant metabolites against Penicillium roqueforti and Aspergillus niger. Among them alpha-Costic acid and ungeremine (3 and 12) are the most promising as potential biofungicide against both fungal strains. They inhibited fungal growth by more than 60% respect to the control at 72 h and this activity persisted also at 96 h. Ungeremine showed MIC90 lower than 0.003 mg/mL after 48 h of incubation and of 0.025 mg/mL at 72 h against P. roqueforti. The MIC90 value for A. niger was 0.2 mg/mL at 48 h for both compounds. The alpha-Costic acid showed generally MIC values at 48 and 72 h higher than ungeremine.
Inuloxins A-D, phytotoxic bi-and tri-cyclic sesquiterpene lactones produced by Inula viscosa: potential for broomrapes and field dodder management.[Pubmed:23137725]
Phytochemistry. 2013 Feb;86:112-20.
Four phytotoxic bi- and tri-cyclic sesquiterpene lactones, named inuloxins A-D, were isolated together with the known alpha-Costic acid, from the aerial parts of Inula viscosa (family Asteraceae), a widespread Mediterranean plant well known for its content of pharmacologically active metabolites. The structures of inuloxins A-D were established by spectroscopic and chemical methods and determined to be: (4E,7R*,8R*,10S*)-3-oxo-germacra-4,11(13)-dien-8beta-12-olide (A), its 11,13-dihydro analogue (B), (5R*,7R*,8R*,10R*)-1,15-methylene-5beta-hydroxy-eudesm-1(15),11(13)-dien-8beta-12 -olide (C), and (7R*,8R*)-1,4-dimethyl-4-hydroxy-secoeudesm-5(10),11(13)-dien-8beta-12-olide (D). The S absolute stereochemistry at C-5 of 5-hydroxyhexan-2-yl side chain of inuloxin D was assigned by applying an advanced Mosher's method. The phytotoxic activity of inuloxins A-D, that of the diazo and monoacetyl derivatives (of inuloxin A and C, resply), as well as that of alpha-Costic acid was evaluated against two parasitic plant species, i.e. crenate broomrape (Orobanche crenata) and field dodder (Cuscuta campestris). Inuloxins A, C and D were the most active on both parasites and caused up to 100% inhibition of the seed germination. Inuloxin B was less active on Cuscuta and completely inactive against Orobanche. The main metabolite alpha-Costic acid had a suppressive effect on the dodder seed germination but had a stimulating action on the broomrape seed germination. These preliminary results allowed to suppose some structure-activity relationships.
