erythrodiol
(3beta)-olean-12-ene-3,28-diol
 
Notes:
Found in grapes, olives, pot marigold (Calendula officinalis) and other plants Erythrodiol 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. Erythrodiol 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, 15522132)
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(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-ol (Click)
CAS Number: 545-48-2Picture of molecule
ECHA EINECS - REACH Pre-Reg: 208-890-4
FDA UNII: 3VWF903FSS
Nikkaji Web: J13.880K
Beilstein Number: 2340203
MDL: MFCD00017294
XlogP3-AA: 7.60 (est)
Molecular Weight: 442.72690000
Formula: C30 H50 O2
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: antioxidants
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 520.50 °C. @ 760.00 mm Hg (est)
Flash Point: 410.00 °F. TCC ( 209.90 °C. ) (est)
logP (o/w): 9.180 (est)
Soluble in:
 water, 0.0001877 mg/L @ 25 °C (est)
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Organoleptic Properties:
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antioxidants
skin conditioning
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Suppliers:
Carbosynth
For experimental / research use only.
Erythrodiol
Coompo
For experimental / research use only.
Erythrodiol from Plants ≥96%
ExtraSynthese
For experimental / research use only.
Erythrodiol (HPLC) ≥97%
Santa Cruz Biotechnology
For experimental / research use only.
Erythrodiol
Sigma-Aldrich
For experimental / research use only.
Erythrodiol
analytical standard
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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
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Safety in Use Information:
Category: antioxidants
Recommendation for erythrodiol usage levels up to:
 not for fragrance use.
 
Recommendation for erythrodiol flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 101761
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 (3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-ol
Chemidplus: 0000545482
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References:
 (3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-ol
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 101761
Pubchem (sid): 135060108
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
HMDB (The Human Metabolome Database): HMDB02360
FooDB: FDB013011
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 grape
Search  Picture
 marigold pot marigold
Search Trop  Picture
 olive oil
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 olive pericarp
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 sunflower shoot
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Synonyms:
(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-ol
(3b)-olean-12-ene-3,28-diol
(3beta)-olean-12-ene-3,28-diol
12-oleanene-3,28-diol
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Articles:
PubMed: Changes in the Triterpenoid Content of Cuticular Waxes during Fruit Ripening of Eight Grape (Vitis vinifera) Cultivars Grown in the Upper Rhine Valley.
PubMed: From a traditional medicinal plant to a rational drug: understanding the clinically proven wound healing efficacy of birch bark extract.
PubMed: Chemical constituents and cytotoxic effect of the main compounds of Lythrum salicaria L.
PubMed: New cytotoxic spirostane saponin and biflavonoid glycoside from the leaves of Acacia saligna (Labill.) H.L. Wendl.
PubMed: Bioactive properties of the main triterpenes found in olives, virgin olive oil, and leaves of Olea europaea.
PubMed: The involvement of β-amyrin 28-oxidase (CYP716A52v2) in oleanane-type ginsenoside biosynthesis in Panax ginseng.
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: 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: 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: Putralone, a novel 10alpha-hydroxy-25-nor D:A friedo-oleanane triterpenoid from Putranjiva roxburghii.
PubMed: Comparison of the triterpenoid content of berries and leaves of lingonberry Vaccinium vitis-idaea from Finland and Poland.
PubMed: Investigation of unsaponifiable matter of plant oils and isolation of eight phytosterols by means of high-speed counter-current chromatography.
PubMed: Natural triterpenes modulate immune-inflammatory markers of experimental autoimmune encephalomyelitis: therapeutic implications for multiple sclerosis.
PubMed: Chemical constituents and allelopathic and antioxidant activities of Alchorneopsis floribunda Müll. Arg. (Euphorbiaceae).
PubMed: CYP716A subfamily members are multifunctional oxidases in triterpenoid biosynthesis.
PubMed: [Synthesis and antitumor activity of betulin, erythrodiol and uvaol aminopropoxy derivatives].
PubMed: Medicago truncatula CYP716A12 is a multifunctional oxidase involved in the biosynthesis of hemolytic saponins.
PubMed: Chemometric classification of the fat residues from the conditioning operations of table olive processing, based on their minor components.
PubMed: Bioactivity-guided study of antiproliferative activities of Salvia extracts.
PubMed: Evaluation of chemical constituents and antinociceptive properties of Myricaria elegans Royle.
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: Antimicrobial and antioxidant effects of phenolic constituents from Klainedoxa gabonensis.
PubMed: Pentacyclic triterpenoids from olive fruit and leaf.
PubMed: Antioxidant and antiatherogenic activities of pentacyclic triterpenic diols and acids.
PubMed: [Immunosuppressive triterpenes from Tetraena mongolica].
PubMed: New hopane triterpene from Dicranostigma leptopodum (Maxim) Fedde.
PubMed: Two new secoiridoid glycosides from the leaves of Olea europaea L.
PubMed: Terpenoids induce cell cycle arrest and apoptosis from the stems of Celastrus kusanoi associated with reactive oxygen species.
PubMed: A new erythrodiol triterpene fatty ester from Scorzonera mongolica.
PubMed: Conferin, potent antioxidant and anti-inflammatory isoflavone from Caragana conferta Benth.
PubMed: Fruit quality and olive leaf and stone addition affect Picual virgin olive oil triterpenic content.
PubMed: Natural triterpenic diols promote apoptosis in astrocytoma cells through ROS-mediated mitochondrial depolarization and JNK activation.
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: Antioxidative action of methanolic extract and buthanolic fraction of Vochysia tucanorum Mart. in the gastroprotection.
PubMed: Cytotoxic activities of extracts and compounds from Viscum coloratum and its transformation products by Rhodobacter sphaeroides.
PubMed: New antibacterial pentacyclic triterpenes from Myricaria elegans Royle. (tamariscineae).
PubMed: Urease inhibitor from Datisca cannabina linn.
PubMed: Biotransformation of beta-amyrin acetate by Rhodobacter sphaeroides.
PubMed: Retraction notice to "Erythrodiol-3-acetate, pentacyclic triterpenoid from Styrax japonica, expressions of matrix metalloproteinase-1,2 in cultured human skin fibroblasts" [J. Ethnopharmacol. 97 (2005) 567-571].
PubMed: Erythrodiol, a natural triterpenoid from olives, has antiproliferative and apoptotic activity in HT-29 human adenocarcinoma cells.
PubMed: Selective solid-phase extraction of a triterpene acid from a plant extract by molecularly imprinted polymer.
PubMed: Oleanolic acid induces prostacyclin release in human vascular smooth muscle cells through a cyclooxygenase-2-dependent mechanism.
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: Tyrosinase inhibitory pentacyclic triterpenes and analgesic and spasmolytic activities of methanol extracts of Rhododendron collettianum.
PubMed: Triterpenes in the hexane extract of leaves of Olea europaea L.: analysis using 13C-NMR spectroscopy.
PubMed: Formation of triterpenoids throughout Olea europaea fruit ontogeny.
PubMed: WITHDRAWN: Erythrodiol-3-acetate isolated from Styrax japonica elicits the inhibition of UV-induced gelatinases B in cultured human keratinocyte cells.
PubMed: Modulation of cytokine secretion by pentacyclic triterpenes from olive pomace oil in human mononuclear cells.
PubMed: Physical, chemical and pharmacological characterization of a new oleogel-forming triterpene extract from the outer bark of birch (betulae cortex).
PubMed: The effect of erythrodiol-3-acetate on the expressions of matrix metalloproteinase-1 and type-1 procollagen caused by ultraviolet irradiated cultured primary old aged human skin fibroblasts.
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: Triterpenoids from Drypetes chevalieri Beille (euphorbiaceae).
PubMed: Four new isoflavonoids from the stem bark of Erythrina variegata.
PubMed: Triterpenic compounds from "orujo" olive oil elicit vasorelaxation in aorta from spontaneously hypertensive rats.
PubMed: WITHDRAWN: The effect of erythrodiol-3-acetate on the expression of matrix metalloproteinase-9 caused by ultraviolet-irradiated cultured human keratinocyte cells.
PubMed: Triterpenoid from Styrax japonica SIEB. et ZUCC, and its effects on the expression of matrix metalloproteinases-1 and type 1 procollagen caused by ultraviolet irradiated cultured primary human skin fibroblasts.
PubMed: Erythrodiol-3-acetate, pentacyclic triterpenoid from Styrax japonica, expressions of matrix metalloproteinase-1,2 in cultured human skin fibroblasts.
PubMed: Effect of dietary high-oleic-acid oils that are rich in antioxidants on microsomal lipid peroxidation in rats.
PubMed: Potential vasorelaxant effects of oleanolic acid and erythrodiol, two triterpenoids contained in 'orujo' olive oil, on rat aorta.
PubMed: 3 Beta-(3,4-dihydroxycinnamoyl)-erythrodiol, a cytotoxic constituent of Zygophyllum geslini collected in the Algerian Sahara.
PubMed: Pentacyclic triterpenoids and their cytotoxicity from the stem bark of Styrax japonica S. et Z.
PubMed: Four new triterpenoids from Maytenus ilicifolia.
PubMed: Saponins from the bark of Nephelium maingayi.
PubMed: Antitumor-promoting constituents from Chaenomeles sinensis KOEHNE and their activities in JB6 mouse epidermal cells.
PubMed: Pentacyclic triterpenoid and saponins from Gambeya boukokoensis.
PubMed: Novel sphingolipids from Conyza canadensis.
PubMed: Pentacyclic triterpenoids from Ilex macropoda.
PubMed: Fatty acid esters of triterpenoids and steroid glycosides from Gambeya africana.
PubMed: Spasmolytic effects of baccharis conferta and some of its constituents.
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: Cytotoxic isoflavones from Erythrina indica.
PubMed: Antiprotozoal activity of the constituents of Conyza filaginoides.
PubMed: Effect of minor components of virgin olive oil on topical antiinflammatory assays.
PubMed: Cytotoxic constituents from Solidago virga-aurea var. gigantea MIQ.
PubMed: Inhibitory effect of some triterpenes from cacti on 32Pi-incorporation into phospholipids of HeLa cells promoted by 12-O-tetradecanoylphorbol-13-acetate.
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: Effect of selected triterpenoids on chronic dermal inflammation.
PubMed: Smooth muscle relaxing flavonoids and terpenoids from Conyza filaginoides.
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: Inhibition of the tumor-promoting action of 12-O-tetradecanoylphorbol-13-acetate by some oleanane-type triterpenoid compounds.
PubMed: [Microbial transformation of erythrodiol].
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