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Capsidiol

CAS# 37208-05-2

Capsidiol

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Chemical structure

Capsidiol

3D structure

Chemical Properties of Capsidiol

Cas No. 37208-05-2 SDF Download SDF
PubChem ID 161937 Appearance Powder
Formula C15H24O2 M.Wt 236.4
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (1R,3R,4S,4aR,6R)-4,4a-dimethyl-6-prop-1-en-2-yl-2,3,4,5,6,7-hexahydro-1H-naphthalene-1,3-diol
SMILES CC1C(CC(C2=CCC(CC12C)C(=C)C)O)O
Standard InChIKey BXXSHQYDJWZXPB-OKNSCYNVSA-N
Standard InChI InChI=1S/C15H24O2/c1-9(2)11-5-6-12-14(17)7-13(16)10(3)15(12,4)8-11/h6,10-11,13-14,16-17H,1,5,7-8H2,2-4H3/t10-,11-,13-,14-,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.
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.
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.

Source of Capsidiol

The leaves of Capsicum annuum L.

Capsidiol Dilution Calculator

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Capsidiol Molarity Calculator

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Preparing Stock Solutions of Capsidiol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.2301 mL 21.1506 mL 42.3012 mL 84.6024 mL 105.753 mL
5 mM 0.846 mL 4.2301 mL 8.4602 mL 16.9205 mL 21.1506 mL
10 mM 0.423 mL 2.1151 mL 4.2301 mL 8.4602 mL 10.5753 mL
50 mM 0.0846 mL 0.423 mL 0.846 mL 1.692 mL 2.1151 mL
100 mM 0.0423 mL 0.2115 mL 0.423 mL 0.846 mL 1.0575 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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References on Capsidiol

The Full-Size ABCG Transporters Nb-ABCG1 and Nb-ABCG2 Function in Pre- and Postinvasion Defense against Phytophthora infestans in Nicotiana benthamiana.[Pubmed:27102667]

Plant Cell. 2016 May;28(5):1163-81.

The sesquiterpenoid Capsidiol is the major phytoalexin produced by Nicotiana and Capsicum species. Capsidiol is produced in plant tissues attacked by pathogens and plays a major role in postinvasion defense by inhibiting pathogen growth. Using virus-induced gene silencing-based screening, we identified two Nicotiana benthamiana (wild tobacco) genes encoding functionally redundant full-size ABCG (PDR-type) transporters, Nb-ABCG1/PDR1 and Nb-ABCG2/PDR2, which are essential for resistance to the potato late blight pathogen Phytophthora infestans Silencing of Nb-ABCG1/2 compromised secretion of Capsidiol, revealing Nb-ABCG1/2 as probable exporters of Capsidiol. Accumulation of plasma membrane-localized Nb-ABCG1 and Nb-ABCG2 was observed at the site of pathogen penetration. Silencing of EAS (encoding 5-epi-aristolochene synthase), a gene for Capsidiol biosynthesis, reduced resistance to P. infestans, but penetration by P. infestans was not affected. By contrast, Nb-ABCG1/2-silenced plants showed reduced penetration defense, indicating that Nb-ABCG1/2 are involved in preinvasion defense against P. infestans Plastidic GGPPS1 (geranylgeranyl diphosphate synthase) was also found to be required for preinvasion defense, thereby suggesting that plastid-produced diterpene(s) are the antimicrobial compounds active in preinvasion defense. These findings suggest that N. benthamiana ABCG1/2 are involved in the export of both antimicrobial diterpene(s) for preinvasion defense and Capsidiol for postinvasion defense against P. infestans.

Variation in capsidiol sensitivity between Phytophthora infestans and Phytophthora capsici is consistent with their host range.[Pubmed:25203155]

PLoS One. 2014 Sep 9;9(9):e107462.

Plants protect themselves against a variety of invading pathogenic organisms via sophisticated defence mechanisms. These responses include deployment of specialized antimicrobial compounds, such as phytoalexins, that rapidly accumulate at pathogen infection sites. However, the extent to which these compounds contribute to species-level resistance and their spectrum of action remain poorly understood. Capsidiol, a defense related phytoalexin, is produced by several solanaceous plants including pepper and tobacco during microbial attack. Interestingly, Capsidiol differentially affects growth and germination of the oomycete pathogens Phytophthora infestans and Phytophthora capsici, although the underlying molecular mechanisms remain unknown. In this study we revisited the differential effect of Capsidiol on P. infestans and P. capsici, using highly pure Capsidiol preparations obtained from yeast engineered to express the Capsidiol biosynthetic pathway. Taking advantage of transgenic Phytophthora strains expressing fluorescent markers, we developed a fluorescence-based method to determine the differential effect of Capsidiol on Phytophtora growth. Using these assays, we confirm major differences in Capsidiol sensitivity between P. infestans and P. capsici and demonstrate that Capsidiol alters the growth behaviour of both Phytophthora species. Finally, we report intraspecific variation within P. infestans isolates towards Capsidiol tolerance pointing to an arms race between the plant and the pathogens in deployment of defence related phytoalexins.

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