uvaol
(3beta)-urs-12-ene-3,28-diol
Identification
| Name | uvaol |
| IUPAC | (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 |
| CAS Number | 545-46-0 |
| EINECS | 208-888-3 |
| FDA UNII | W599R31ROT |
| Molecular Formula | C30 H50 O2 |
| Molecular Weight | 442.72690000 |
| MDL Number | MFCD00009620 |
| Nikkaji Number | J14.120H |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 523.70 °C. @ 760.00 mm Hg (est) |
| Flash Point | 413.00 °F. TCC ( 211.60 °C. ) (est) |
| logP (o/w) | 9.130 (est) |
| Soluble in | water, 0.0002014 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for uvaol usage levels up to | not for fragrance use. |
| Recommendation for uvaol flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
(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
(3beta)-
urs-12-ene-3,28-diol
urs-12-ene-3beta,28-diol
PubMed:
Chemical of Vitex trifolia.
PubMed:
[Chemical constituents from Euphorbia lunulata].
PubMed:
Studies on cytotoxic constituents from the leaves of Elaeagnus oldhamii Maxim. in non-small cell lung cancer A549 cells.
PubMed:
[Chemical constituents from the roots of Ilex pubescens].
PubMed:
New cytotoxic cycloartane triterpene from Cassia italica aerial parts.
PubMed:
A new antioxidant stilbene and other constituents from the stem bark of Morus nigra L.
PubMed:
Bioactive properties of the main triterpenes found in olives, virgin olive oil, and leaves of Olea europaea.
PubMed:
Time course of pentacyclic triterpenoids from fruits and leaves of olive tree (Olea europaea L.) cv. Picual and cv. Cornezuelo during ripening.
PubMed:
[Chemical constituents of Gentiana rhodantha].
PubMed:
[Chemical constituents and their antitumor cytotoxic activity in leaves of Ilex centrochinensis].
PubMed:
A rapid method to determine sterol, erythrodiol, and uvaol concentrations in olive oil.
PubMed:
Changes of the wax contents in mixtures of olive oils as determined by gas chromatography with a flame ionization detector.
PubMed:
Triterpenoid content of berries and leaves of bilberry Vaccinium myrtillus from Finland and Poland.
PubMed:
Triterpenoid profile of flower and leaf cuticular waxes of heather Calluna vulgaris.
PubMed:
Fast separation of triterpenoids by supercritical fluid chromatography/evaporative light scattering detector.
PubMed:
Sterols and triterpene diols in olive oil as indicators of variety and degree of ripening.
PubMed:
Study of skin anti-ageing and anti-inflammatory effects of dihydroquercetin, natural triterpenoids, and their synthetic derivatives.
PubMed:
Characterisation and phenolic profiles of two rare olive oils from southern Tunisia: Dhokar and Gemri-Dhokar cultivars.
PubMed:
DIOL triterpenes block profibrotic effects of angiotensin II and protect from cardiac hypertrophy.
PubMed:
Efficacy of bioactive compounds from extra virgin olive oil to modulate atherosclerosis development.
PubMed:
Anti-Helicobacter pylori activity of the methanolic extract of Geum iranicum and its main compounds.
PubMed:
Comparison of the triterpenoid content of berries and leaves of lingonberry Vaccinium vitis-idaea from Finland and Poland.
PubMed:
Chemical constituents and allelopathic and antioxidant activities of Alchorneopsis floribunda Müll. Arg. (Euphorbiaceae).
PubMed:
Cloning, expression, characterization and inhibition studies on trypanothione synthetase, a drug target enzyme, from Leishmania donovani.
PubMed:
CYP716A subfamily members are multifunctional oxidases in triterpenoid biosynthesis.
PubMed:
[Synthesis and antitumor activity of betulin, erythrodiol and uvaol aminopropoxy derivatives].
PubMed:
[Studies on the chemical constituents of Coleus forskohlii transplanted in Tongcheng and their antitumor activity].
PubMed:
Inhibitory effects of constituents from Morus alba var. multicaulis on differentiation of 3T3-L1 cells and nitric oxide production in RAW264.7 cells.
PubMed:
Chemometric classification of the fat residues from the conditioning operations of table olive processing, based on their minor components.
PubMed:
Antibacterial properties of compounds isolated from Carpobrotus edulis.
PubMed:
Antioxidant, antiproliferative, and pro-apoptotic capacities of pentacyclic triterpenes found in the skin of olives on MCF-7 human breast cancer cells and their effects on DNA damage.
PubMed:
Pentacyclic triterpenoids from olive fruit and leaf.
PubMed:
Antioxidant and antiatherogenic activities of pentacyclic triterpenic diols and acids.
PubMed:
Constituents of Carpobrotus edulis inhibit P-glycoprotein of MDR1-transfected mouse lymphoma cells.
PubMed:
Fruit quality and olive leaf and stone addition affect Picual virgin olive oil triterpenic content.
PubMed:
A new labdane diterpene from Vitex cauliflora Moldenke from the Madagascar rainforest.
PubMed:
Natural triterpenic diols promote apoptosis in astrocytoma cells through ROS-mediated mitochondrial depolarization and JNK activation.
PubMed:
In vitro antileishmanial, antiplasmodial and cytotoxic activities of phenolics and triterpenoids from Baccharis dracunculifolia D. C. (Asteraceae).
PubMed:
Triterpenic content and chemometric analysis of virgin olive oils from forty olive cultivars.
PubMed:
Fast and selective determination of triterpenic compounds in olive leaves by liquid chromatography-tandem mass spectrometry with multiple reaction monitoring after microwave-assisted extraction.
PubMed:
Steroids, alkaloids, and coumarins from Gelsemium sempervirens.
PubMed:
A new monoterpene alkaloid and other constituents of Plumeria acutifolia.
PubMed:
[Studies on triterpenoid constituents in leaf of Ilex pernyi].
PubMed:
[Studies on chemical constituents of in herb Pyrola calliatha].
PubMed:
How heating affects extra virgin olive oil quality indexes and chemical composition.
PubMed:
Ultrasound-assisted extraction and silylation prior to gas chromatography-mass spectrometry for the characterization of the triterpenic fraction in olive leaves.
PubMed:
Triterpenes in the hexane extract of leaves of Olea europaea L.: analysis using 13C-NMR spectroscopy.
PubMed:
Antimicrobial activity of oleanolic acid from Salvia officinalis and related compounds on vancomycin-resistant enterococci (VRE).
PubMed:
Formation of triterpenoids throughout Olea europaea fruit ontogeny.
PubMed:
Modulation of cytokine secretion by pentacyclic triterpenes from olive pomace oil in human mononuclear cells.
PubMed:
Analysis of unsaponifiable compounds of edible oils by automated on-line coupling reversed-phase liquid chromatography-gas chromatography using the through oven transfer adsorption desorption interface.
PubMed:
Triterpenic compounds from "orujo" olive oil elicit vasorelaxation in aorta from spontaneously hypertensive rats.
PubMed:
Triterpenoids from Brazilian Ilex species and their in vitro antitrypanosomal activity.
PubMed:
Cardiotonic and antidysrhythmic effects of oleanolic and ursolic acids, methyl maslinate and uvaol.
PubMed:
Four new triterpenoids from Maytenus ilicifolia.
PubMed:
Chemical constituents from the leaves of Psidium guajava.
PubMed:
[Studies on chemical components of Gentiana tizuensis Franch. (I)].
PubMed:
Inhibitory activity of minor polyphenolic and nonpolyphenolic constituents of olive oil against in vitro low-density lipoprotein oxidation.
PubMed:
Antimicrobial triterpenes from Debregeasia salicifolia.
PubMed:
Effect of five triterpenoid compounds isolated from leaves of Diospyros kaki on stimulus-induced superoxide generation and tyrosyl phosphorylation in human polymorphonuclear leukocytes.
PubMed:
Microbial transformation of cadina-4,10(15)-dien-3-one, aromadendr-1(10)-en-9-one and methyl ursolate by Mucor plumbeus ATCC 4740.
PubMed:
Constituents of Compositae plants III. Anti-tumor promoting effects and cytotoxic activity against human cancer cell lines of triterpene diols and triols from edible chrysanthemum flowers.
PubMed:
[Nonpolar components of the leaves of Philadelphus coronarius L].
PubMed:
Cytotoxic triterpenes from Crataegus pinnatifida.
PubMed:
Protective effects of triterpene compounds against the cytotoxicity of cadmium in HepG2 cells.
PubMed:
Inhibitory effect of triterpenes from Crataegus pinatifida on HIV-I protease.
PubMed:
Chitin synthase II inhibitory activity of ursolic acid, isolated from Crataegus pinnatifida.
PubMed:
Terpenoids of Syzygium formosanum.
PubMed:
Synthesis and anti-ulcer activity of new derivatives of glycyrrhetic, oleanolic and ursolic acids.
PubMed:
Validated method for quantitation and identification of 4,4-desmethylsterols and triterpene diols in plant oils by thin-layer chromatography-high resolution gas chromatography-mass spectrometry.
PubMed:
Inhibitory effect of Di- and trihydroxy triterpenes from the flowers of compositae on 12-O-tetradecanoylphorbol-13-acetate-induced inflammation in mice.
PubMed:
Synthesis and antiulcer activity of uvaol hemiphthalate derivatives.
PubMed:
Effects of Ursolic Acid and its Analogues on Soybean 15-Lipoxygenase Activity and the Proliferation Rate of A human Gastric Tumour Cell Line.
PubMed:
The effects of 10 triterpenoid compounds on experimental liver injury in mice.
PubMed:
Effects of xanthone glycoside on ephedrine-induced biting behavior and motor activity.
PubMed:
Determination of sterols, erythrodiol, uvaol and alkanols in olive oils using combined solid-phase extraction, high-performance liquid chromatographic and high-resolution gas chromatographic techniques.
PubMed:
Inhibition of human leucocyte elastase by ursolic acid. Evidence for a binding site for pentacyclic triterpenes.
PubMed:
[Plant from New-Caledonia. Alkaloids of Melodinus reticulatus].
PubMed:
Tumor inhibitory agents from Vauquelinia corymbosa (Rosaceae).
PubMed:
A new triterpenoid lactone, alpha-amyrin and uvaol from Helichrysum italicum.
PubMed:
[Ursolic acid and uvaol as contents of Rhododendron ponticum].
PubMed:
[A new natural triterpenic lactone, alpha-amyrin and uvaol from Helichrysum italicum (G. Don)].