Macrocarpal ACAS# 132951-90-7 |
- Macrocarpal B
Catalog No.:BCN6236
CAS No.:142698-60-0
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 132951-90-7 | SDF | Download SDF |
| PubChem ID | 454457 | Appearance | Yellow powder |
| Formula | C28H40O6 | M.Wt | 472.6 |
| Type of Compound | Sesquiterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | 5-[(1R)-1-[(1aR,4R,4aR,7S,7aS,7bR)-4-hydroxy-1,1,4,7-tetramethyl-1a,2,3,4a,5,6,7a,7b-octahydrocyclopropa[h]azulen-7-yl]-3-methylbutyl]-2,4,6-trihydroxybenzene-1,3-dicarbaldehyde | ||
| SMILES | CC(C)CC(C1=C(C(=C(C(=C1O)C=O)O)C=O)O)C2(CCC3C2C4C(C4(C)C)CCC3(C)O)C | ||
| Standard InChIKey | IBLPTYJTKWQCDX-MOTAWSDJSA-N | ||
| Standard InChI | InChI=1S/C28H40O6/c1-14(2)11-19(20-24(32)15(12-29)23(31)16(13-30)25(20)33)27(5)9-7-18-22(27)21-17(26(21,3)4)8-10-28(18,6)34/h12-14,17-19,21-22,31-34H,7-11H2,1-6H3/t17-,18-,19+,21-,22-,27-,28-/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. | ||
| Description | 1. Macrocarpal A has cytotoxic activity. 2. Macrocarpal A has antibacterial activity. 3. Macrocarpal A is the key component that stimulates the synthesis of ceramide in the stratum corneum.. |
| Targets | Antifection |
Macrocarpal A Dilution Calculator
Macrocarpal A Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.116 mL | 10.5798 mL | 21.1595 mL | 42.3191 mL | 52.8989 mL |
| 5 mM | 0.4232 mL | 2.116 mL | 4.2319 mL | 8.4638 mL | 10.5798 mL |
| 10 mM | 0.2116 mL | 1.058 mL | 2.116 mL | 4.2319 mL | 5.2899 mL |
| 50 mM | 0.0423 mL | 0.2116 mL | 0.4232 mL | 0.8464 mL | 1.058 mL |
| 100 mM | 0.0212 mL | 0.1058 mL | 0.2116 mL | 0.4232 mL | 0.529 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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Intestinal permeability of antivirus constituents from the fruits of Eucalyptus globulus Labill. in Caco-2 Cell Model.[Pubmed:17118653]
Bioorg Med Chem Lett. 2007 Feb 15;17(4):1107-11.
The uptake and transepithelial transport of the three main constituents Macrocarpal A (M-A), macrocarpal B (M-B), and cypellocarpa C (Cy-C) from the fruits of Eucalyptus globulus Labill. were investigated. Monolayers of the human intestinal epithelial cancer cell line Caco-2 were incubated with M-A, M-B, and Cy-C to model its intestinal absorption and transport, respectively. The determination of compounds was performed by HPLC. The apparent permeability coefficients (P(app)) for M-A, M-B, and Cy-C in the apical-to-basolateral direction of a Caco-2 monolayer were (1.70+/-0.06)x10(-6), (1.99+/-0.10)x10(-6), and (6.08+/-0.41)x10(-6)cm/s, respectively. In the presence of iodoacetamide, the P(app) of Cy-C were both reducted in apical-to-basolateral and basolateral-to-apical directions. M-A and M-B appear to accumulate in the epithelial cells. The intestinal absorption of M-A, M-B, and Cy-C was passive diffusion as the dominating process and Cy-C was partly ATP-dependent.
Eucalyptus increases ceramide levels in keratinocytes and improves stratum corneum function.[Pubmed:21696405]
Int J Cosmet Sci. 2012 Feb;34(1):17-22.
The objectives of this study were to identify a plant extract that would improve stratum corneum functions and to elucidate the mechanism(s) involved. Based on the information that stratum corneum functions depend on the level of ceramide in the stratum corneum, we identified a Eucalyptus extract that was able to increase the level of ceramide in human keratinocytes in culture and in human stratum corneum and that improves the stratum corneum water holding and barrier functions. Addition of the Eucalyptus extract to human keratinocytes in culture increased the level of ceramide in a dose-dependent manner and also increased the biosynthesis of ceramide, glucosylceramide and sphingomyelin. Topical application of the Eucalyptus extract on the dry skin of human subjects induced by acetone and diethylether treatment resulted in a significant increase in ceramide level in the stratum corneum, a significant improvement in its water-holding function and an improvement in its barrier function. The addition of Macrocarpal A, one of the main components of the Eucalyptus extract, to human keratinocytes in culture increased the level of ceramide and the mRNA expression of serine palmitoyltransferase, acid sphingomyelinase, neutral sphingomyelinase, glucosylceramide synthase and glucocerebrosidase in a dose-dependent manner. Our results indicate that the increased content of ceramides in the stratum corneum may underlie the therapeutic effect of the Eucalyptus extract. Our results also indicate the possibility that Macrocarpal A is the key component that stimulates the synthesis of ceramide in the stratum corneum.
Semisynthesis of macrocarpal C and analogues by selective dehydration of macrocarpal A or B.[Pubmed:24261967]
J Nat Prod. 2013 Dec 27;76(12):2346-9.
Macrocarpals A and C are structurally related compounds that have been extracted from different Eucalyptus species. Although macrocarpal C is of biological interest, its isolation in pure form is difficult to achieve. We report herein an efficient method for the semisynthesis of macrocarpal C by selective exo-dehydration of another member of the macrocarpal family, Macrocarpal A. We also report the semisynthesis of three new macrocarpal structures derived from either Macrocarpal A or B.
Cytotoxic activity of acyl phloroglucinols isolated from the leaves of Eucalyptus cinerea F. Muell. ex Benth. cultivated in Egypt.[Pubmed:24986654]
Sci Rep. 2014 Jul 2;4:5410.
Two acyl phloroglucinol compounds namely; Sideroxylonal B (1) and Macrocarpal A (2) were isolated from the Sideroxylonal-Rich Extract (SRE) of the juvenile leaves of Eucalyptus cinerea; F. Muell. ex Benth cultivated in Egypt. Identification of the isolated compounds was established on the basis of physico-chemical properties and spectral analysis (1D & 2D NMR). The two compounds were isolated for the first time from this species. The SRE alongside with the isolated compounds were tested against three human cancer cell lines; MCF7 (breast carcinoma cell line), HEP2 (laryngeal carcinoma), CaCo (colonic adenocarcinoma) and one type of normal human cell line;10 FS (fibroblast cells). The SRE, (1), and (2) showed cytotoxic activity with IC(5)(0) 13.6 +/- 0.62, 7.2 +/- 0.5, 14.8 +/- 0.55 mug mL-1 against HEP2 respectively, 11.6 +/- 0.47, 4 +/- 0.36, 11.4 +/- 0.45 mug mL-1 against CaCo, respectively, and 8.6 +/- 0.29, 4.4 +/- 0.25, and 7.8 +/- 0.3 mug mL-1 against MCF7, respectively. Meanwhile, the (SRE) together with (1) and (2) exhibited low cytotoxicity against normal cell line 10 FS, with IC(5)(0) 55.4 +/- 1.4, 43 +/- 0.8 and 50.1 +/- 1.12 mug mL-1, respectively. The antiprofilerative activity of the tested compounds was evaluated. The cell cycle profile of cells treated with Sideroxylonal-B and Macrocarpal-A indicates possible S-phase specific effects.
