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3-Acetoxy-8(17),13E-labdadien-15-oic acid

CAS# 63399-37-1

3-Acetoxy-8(17),13E-labdadien-15-oic acid

Catalog No. BCN1390----Order now to get a substantial discount!

Product Name & Size Price Stock
3-Acetoxy-8(17),13E-labdadien-15-oic acid: 5mg $690 In Stock
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Quality Control of 3-Acetoxy-8(17),13E-labdadien-15-oic acid

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Chemical structure

3-Acetoxy-8(17),13E-labdadien-15-oic acid

3D structure

Chemical Properties of 3-Acetoxy-8(17),13E-labdadien-15-oic acid

Cas No. 63399-37-1 SDF Download SDF
PubChem ID 13858192 Appearance Powder
Formula C22H34O4 M.Wt 362.5
Type of Compound Diterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (E)-5-[(1S,4aR,6S,8aR)-6-acetyloxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid
SMILES CC(=CC(=O)O)CCC1C(=C)CCC2C1(CCC(C2(C)C)OC(=O)C)C
Standard InChIKey OMNJRQNCWHCCBZ-BULWIKRESA-N
Standard InChI InChI=1S/C22H34O4/c1-14(13-20(24)25)7-9-17-15(2)8-10-18-21(4,5)19(26-16(3)23)11-12-22(17,18)6/h13,17-19H,2,7-12H2,1,3-6H3,(H,24,25)/b14-13+/t17-,18-,19-,22+/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.
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 3-Acetoxy-8(17),13E-labdadien-15-oic acid

The rhizoma of Cibotium barometz (L.) J.Sm.

Biological Activity of 3-Acetoxy-8(17),13E-labdadien-15-oic acid

Descriptionent-3-Acetoxy-labda-8(17),13-dien-15-oic acid have vasorelaxant and hypotensive actions, the mechanisms underlying the cardiovascular actions of the labdane involve the activation of the endothelial NO-cGMP pathway, the opening of K+ channels and the alteration on Ca2+ mobilization.
TargetsCalcium Channel | cAMP | Potassium Channel | NO
In vivo

Mechanisms underlying the vascular and hypotensive actions of the labdane ent-3-acetoxy-labda-8(17),13-dien-15-oic acid.[Pubmed: 24463178 ]

Eur J Pharmacol. 2014 Mar 5;726:66-76.

We investigated the mechanisms underlying the vasorelaxant and hypotensive actions of the labdane-type diterpene ent-3-acetoxy-labda-8(17),13-dien-15-oic acid (3-Acetoxy-8(17),13E-labdadien-15-oic acid,labda-15-oic acid).
METHODS AND RESULTS:
Vascular reactivity experiments were performed in aortic rings isolated from male Wistar rats. cAMP and cGMP were measured by enzyme immunoassay (EIA) whereas nitrate measurement was performed by chemiluminescence. Nitric oxide (NO) concentration ([NO]c) was measured in endothelial cells by flow cytometry. The cytosolic calcium concentration ([Ca2+]c) in vascular smooth muscle cells (VSMC) was measured by confocal microscopy. Blood pressure measurements were performed in conscious rats. Labda-15-oic acid inhibited the contraction induced by phenylephrine and serotonin in either endothelium-intact or endothelium-denuded rat aortic rings. The labdane significantly reduced CaCl2-induced contraction in a Ca2+-free solution containing KCl or phenylephrine. Labda-15-oic acid (0.1–300 μmol/l) concentration-dependently relaxed endothelium-intact and endothelium-denuded aortas pre-contracted with either phenylephrine or KCl. In endothelium-intact rings, the relaxation induced by labda-15-oic acid was affected by L-NAME, 7-nitroindazole, ODQ, hemoglobin, Rp-8-Br-Pet-cGMPS and thapsigargin. Blockade of K+ channels with 4-aminopyridine, apamin, charybdotoxin and glibenclamide affected the relaxation induced by labda-15-oic acid. The labdane increased cGMP and nitrate levels but did not affect cAMP levels in endothelium-intact aortas. Labda-15-oic acid increased [NO]c in endothelial cells and decreased [Ca2+]c in VSMC. The hypotension induced by intravenous administration of labda-15-oic acid (0.3–3 mg/kg) was partially reduced by L-NAME.
CONCLUSIONS:
In conclusion, the mechanisms underlying the cardiovascular actions of the labdane involve the activation of the endothelial NO-cGMP pathway, the opening of K+ channels and the alteration on Ca2+ mobilization.

3-Acetoxy-8(17),13E-labdadien-15-oic acid Dilution Calculator

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Preparing Stock Solutions of 3-Acetoxy-8(17),13E-labdadien-15-oic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.7586 mL 13.7931 mL 27.5862 mL 55.1724 mL 68.9655 mL
5 mM 0.5517 mL 2.7586 mL 5.5172 mL 11.0345 mL 13.7931 mL
10 mM 0.2759 mL 1.3793 mL 2.7586 mL 5.5172 mL 6.8966 mL
50 mM 0.0552 mL 0.2759 mL 0.5517 mL 1.1034 mL 1.3793 mL
100 mM 0.0276 mL 0.1379 mL 0.2759 mL 0.5517 mL 0.6897 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 3-Acetoxy-8(17),13E-labdadien-15-oic acid

Mechanisms underlying the vascular and hypotensive actions of the labdane ent-3-acetoxy-labda-8(17),13-dien-15-oic acid.[Pubmed:24463178]

Eur J Pharmacol. 2014 Mar 5;726:66-76.

We investigated the mechanisms underlying the vasorelaxant and hypotensive actions of the labdane-type diterpene ent-3-acetoxy-labda-8(17),13-dien-15-oic acid (labda-15-oic acid). Vascular reactivity experiments were performed in aortic rings isolated from male Wistar rats. cAMP and cGMP were measured by enzyme immunoassay (EIA) whereas nitrate measurement was performed by chemiluminescence. Nitric oxide (NO) concentration ([NO]c) was measured in endothelial cells by flow cytometry. The cytosolic calcium concentration ([Ca2+]c) in vascular smooth muscle cells (VSMC) was measured by confocal microscopy. Blood pressure measurements were performed in conscious rats. Labda-15-oic acid inhibited the contraction induced by phenylephrine and serotonin in either endothelium-intact or endothelium-denuded rat aortic rings. The labdane significantly reduced CaCl2-induced contraction in a Ca2+-free solution containing KCl or phenylephrine. Labda-15-oic acid (0.1-300 mumol/l) concentration-dependently relaxed endothelium-intact and endothelium-denuded aortas pre-contracted with either phenylephrine or KCl. In endothelium-intact rings, the relaxation induced by labda-15-oic acid was affected by L-NAME, 7-nitroindazole, ODQ, hemoglobin, Rp-8-Br-Pet-cGMPS and thapsigargin. Blockade of K+ channels with 4-aminopyridine, apamin, charybdotoxin and glibenclamide affected the relaxation induced by labda-15-oic acid. The labdane increased cGMP and nitrate levels but did not affect cAMP levels in endothelium-intact aortas. Labda-15-oic acid increased [NO]c in endothelial cells and decreased [Ca2+]c in VSMC. The hypotension induced by intravenous administration of labda-15-oic acid (0.3-3 mg/kg) was partially reduced by L-NAME. In conclusion, the mechanisms underlying the cardiovascular actions of the labdane involve the activation of the endothelial NO-cGMP pathway, the opening of K+ channels and the alteration on Ca2+ mobilization.

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