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OLEAN-12-ENE-3B,28-DIOL

Alias: Uvaol
Cat No.:V34385 Purity: ≥98%
Uvaol is a triterpenoid found in olives and virgin olive oil that has anti~inflammatory and antioxidant effects.
OLEAN-12-ENE-3B,28-DIOL
OLEAN-12-ENE-3B,28-DIOL Chemical Structure CAS No.: 545-46-0
Product category: Natural Products
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
100mg
Other Sizes
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Product Description
Uvaol is a triterpenoid found in olives and virgin olive oil that has anti~inflammatory and antioxidant effects. Uvaol attenuates pleurisy and eosinophilic inflammation in ovalbumin-sensitized mice.
Uvaol (Urs-12-ene-3,28-diol) is a pentacyclic triterpene present in olives and virgin olive oil. It has been shown to possess anti-inflammatory properties and antioxidant effects. However, prior to this study, no investigations had demonstrated its potential effects on allergic inflammation. This study aimed to evaluate the anti-inflammatory effects of Uvaol in mouse models of allergy characterized by eosinophil-dominant inflammation. [1]
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Uvaol did not prevent the increase in intracellular reactive oxygen species levels in bronchoalveolar lavage (BAL) fluid cells at 48 h post-allergen challenge, as measured by flow cytometry using DCF-DA fluorescence. The reactive oxygen species generation in cells from BAL was significantly higher after OVA challenge compared to saline stimulus, but Uvaol treatment (100, 200, 500 μmol/kg, p.o.) showed no inhibitory effect on ROS levels. [1]
ln Vivo
In the allergic pleurisy model (Swiss mice sensitized with OVA/aluminum hydroxide on days 0 and 7, then challenged intrapleurally with OVA 12.5 μg/cavity on day 14), oral administration of Uvaol (100, 200, 500 μmol/kg) 1 h before challenge significantly decreased total leukocyte accumulation in the pleural cavity. Specifically, eosinophil influx was reduced (statistical significance indicated), and IL-5 levels in pleural effluent were decreased from 302.51±32.22 pg/ml (OVA control) to 167.60±29.32, 128.91±13.49, and 51.70±7.3 pg/ml respectively. Dexamethasone (10 μmol/kg i.p.) reduced IL-5 to 37.28±7.70 pg/ml. [1]
In the allergic asthma model (sensitized with OVA on days 0 and 14, then intranasal OVA challenges 25 μg/25 μl on days 21,22,23), Uvaol (200 and 500 μmol/kg, p.o. 1 h before each challenge) significantly decreased total leukocyte and eosinophil counts in bronchoalveolar lavage fluid at 48 h after last challenge. IL-5 levels in BAL fluid were reduced from 205.4±23.66 pg/ml (OVA control) to 63.64±4.98 pg/ml (100 μmol/kg), 120.5±23.61 pg/ml (200 μmol/kg), and 88.79±17.47 pg/ml (500 μmol/kg). Dexamethasone decreased total leukocytes by 68% and eosinophils by 90%. [1]
In lung tissue histopathology, Uvaol (100, 200, 500 μmol/kg) significantly reduced perivascular and peribronchiolar leukocyte infiltration, mucus hyper-secretion (PAS-positive cells), and alveolar collapse percentage compared to OVA-challenged controls. The inflammatory score and mucus production were decreased. Morphometric analysis showed that OVA challenge increased alveolar collapse, and Uvaol treatment at all doses led to a significant reduction in alveolar collapse. Dexamethasone caused a slight reduction (21.4%±4.59%) in alveolar collapse. [1]
Cell Assay
For measurement of intracellular reactive oxygen species, cells from bronchoalveolar lavage fluid were washed with PBS, counted, and then incubated with 5 μM DCF-DA for 30 min at 37°C. The fluorescence was determined at 488 nm excitation and 525 nm emission by flow cytometry. The results showed that Uvaol treatment (100, 200, 500 μmol/kg, p.o. given to animals prior to cell collection) did not prevent the increase in reactive oxygen species levels in BAL cells at 48 h post-OVA challenge compared to the OVA-challenged control group. [1]
Animal Protocol
For the allergic pleurisy model: Male Swiss mice (25-30 g) were immunized subcutaneously on days 0 and 7 with 0.2 ml of solution containing 50 μg ovalbumin adsorbed to 5 mg aluminum hydroxide. On day 14, sensitized mice were challenged intrapleurally with 12.5 μg ovalbumin in 50 μl sterile saline. Uvaol was dissolved in 2% DMSO in sterile saline and administered orally (100, 200, or 500 μmol/kg) 60 min before allergen challenge. Control animals received vehicle (2% DMSO in saline) or dexamethasone (10 μmol/kg, intraperitoneal) 60 min before challenge. Mice were euthanized 24 h later, and the thoracic cavity was washed with 1 ml PBS containing 10 mM EDTA for cell and cytokine analysis. [1]
For the allergic asthma model: Mice were immunized subcutaneously on day 0 and boosted intraperitoneally 14 days later with 50 μg ovalbumin adsorbed to 5 mg aluminum hydroxide in 200 μl sterile saline. Intranasal ovalbumin challenges (25 μg/25 μl saline) were administered on days 21, 22, and 23 under xylazine (5 mg/kg, i.p.) and ketamine (35 mg/kg, i.p.) anesthesia. Uvaol (100, 200, 500 μmol/kg) or vehicle (2% DMSO in saline) was given by gavage 1 h before each allergen challenge. Dexamethasone (10 μmol/kg, i.p.) was used as positive control. Forty-eight hours after the last challenge, mice were killed, and bronchoalveolar lavage was performed twice with 1 ml PBS containing 10 mM EDTA via a tracheal cannula. Lungs were resected for histopathology (fixed in 10% formalin, paraffin-embedded, sectioned at 5 μm, stained with H&E, PAS, and elastic stain). Morphometric analysis was performed using a point-counting technique. [1]
References

[1]. Uvaol attenuates pleuritis and eosinophilic inflammation in ovalbumin-induced allergy in mice. Eur J Pharmacol. 2016 Jun 5;780:232-42.

Additional Infomation
Uvarol is a triterpenoid compound that acts as a metabolite. It has been reported to be found in Callicarpa limonata, Salvia splendens, and other organisms with relevant data.
Uvaol is a pentacyclic triterpene (Urs-12-ene-3,28-diol) found in olives and virgin olive oil. This study is the first to demonstrate that Uvaol attenuates eosinophilic allergic inflammation, mucus secretion, and alveolar collapse in ovalbumin-sensitized and challenged mice. The anti-allergic effect appears to involve reduction of IL-5 concentration. Uvaol exhibited anti-inflammatory activity without affecting reactive oxygen species levels in leukocytes, suggesting an ROS-independent mechanism. The compound may represent a potential candidate for treating allergic inflammation, including asthma. [1]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C30H50O2
Molecular Weight
442.7168
Exact Mass
442.381
Elemental Analysis
C, 81.39; H, 11.38; O, 7.23
CAS #
545-46-0
PubChem CID
92802
Appearance
White to off-white solid powder
Density
1.1±0.1 g/cm3
Boiling Point
523.7±50.0 °C at 760 mmHg
Melting Point
223-225ºC(lit.)
Flash Point
211.6±24.7 °C
Vapour Pressure
0.0±3.1 mmHg at 25°C
Index of Refraction
1.550
LogP
9.13
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Heavy Atom Count
32
Complexity
799
Defined Atom Stereocenter Count
10
SMILES
O([H])[C@@]1([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@]([H])(C1(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@@]1(C([H])([H])[H])[C@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]4(C([H])([H])O[H])C([H])([H])C([H])([H])[C@@]([H])(C([H])([H])[H])[C@]([H])(C([H])([H])[H])[C@@]4([H])C3=C([H])C([H])([H])[C@@]12[H]
InChi Key
XUARCIYIVXVTAE-ZAPOICBTSA-N
InChi Code
InChI=1S/C30H50O2/c1-19-10-15-30(18-31)17-16-28(6)21(25(30)20(19)2)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h8,19-20,22-25,31-32H,9-18H2,1-7H3/t19-,20+,22+,23-,24+,25+,27+,28-,29-,30-/m1/s1
Chemical Name
(3S,4aR,6aR,6bS,8aS,11R,12S,12aS,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picen-3-ol
Synonyms
Uvaol
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
Ethanol : ~10 mg/mL (~22.59 mM)
DMSO : ~2 mg/mL (~4.52 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 1 mg/mL (2.26 mM) in 10% EtOH + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 10.0 mg/mL clear EtOH stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 1 mg/mL (2.26 mM) (saturation unknown) in 10% EtOH + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 10.0 mg/mL clear EtOH stock solution to 900 μL of corn oil and mix well.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.2588 mL 11.2938 mL 22.5876 mL
5 mM 0.4518 mL 2.2588 mL 4.5175 mL
10 mM 0.2259 mL 1.1294 mL 2.2588 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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