| 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 |
| CAS Number: | 545-46-0 |  3D/inchi
|
| ECHA EINECS - REACH Pre-Reg: | 208-888-3 |
| FDA UNII: | W599R31ROT |
| Nikkaji Web: | J14.120H |
| MDL: | MFCD00009620 |
| XlogP3-AA: | 7.40 (est) |
| Molecular Weight: | 442.72690000 |
| Formula: | C30 H50 O2 |
| BioActivity Summary: | listing |
| NMR Predictor: | Predict (works with chrome, Edge or firefox) |
Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
| Preferred SDS: View |
| |
| Hazards identification |
| |
| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
| |
| Pictogram | |
| |
| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
|
Not determined
|
| Dermal Toxicity: |
|
Not determined
|
| Inhalation Toxicity: |
|
Not determined
|
Safety in Use Information:
| 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.
|
Safety References:
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :92802 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| (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 |
| Chemidplus:0000545460 |
References:
| | (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 |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 92802 |
| Pubchem (sid): | 135050099 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
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 |
Articles:
| 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)]. |
|
from vauquelinia corymbosa (rosaceae). Constit. of olive oil and Osmanthus fragrans (sweet osmanthus)
Uvaol is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Uvaol exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. (PMID: 17292619)
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