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taraxerol

natural substances and extractives
2D:
3D:
CAS Number: 127-22-0
FDA UNII: A32778O852
Category: natural substances and extractives
IUPAC Name: taraxerol
InChI : InChI=1/C30H50O/c1-25(2)17-18-27(5)13-9-21-29(7)14-10-20-26(3,4)24(31)12-16-28(20,6)22(29)11-15-30(21,8)23(27)19-25/h9,20,22-24,31H,10-19H2,1-8H3/t20-,22+,23+,24-,27-,28-,29-,30+/m0/s1
Std.InChI: InChI=1S/C30H50O/c1-25(2)17-18-27(5)13-9-21-29(7)14-10-20-26(3,4)24(31)12-16-28(20,6)22(29)11-15-30(21,8)23(27)19-25/h9,20,22-24,31H,10-19H2,1-8H3/t20-,22+,23+,24-,27-,28-,29-,30+/m0/s1
InChIKey : GGGUGZHBAOMSFJ-GADYQYKKBI
Std.InChIKey: GGGUGZHBAOMSFJ-GADYQYKKSA-N
SMILES : C[C@]12CCC(C[C@H]1[C@@]3(CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4(C3=CC2)C)(C)C)O)C)C)(C)C
MDL: MFCD13186859
Molar Refractivity : 131.92 ± 0.4 cm3 (est)
Parachor : 1054.8 ± 6.0 cm3 (est)
Index of Refraction : 1.539 ± 0.03 (est)
Surface Tension : 39.4 ± 5.0 dyne/cm (est)
Density : 1.01 ± 0.1 g/cm3 (est)
Polarizability : 52.29 ± 0.5 10-24cm3 (est)

US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:

Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
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Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search

Physical Properties:

Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 283.50 °C. @ 760.00 mm Hg
Boiling Point: 490.70 °C. @ 760.00 mm Hg (est)
Flash Point: 424.00 °F. TCC ( 217.70 °C. ) (est)
logP (o/w): 11.060 (est)
Soluble in:
water, 9.552e-005 mg/L @ 25 °C (est)

Cosmetic Information:

None found

Suppliers:

Alfa Biotechnology
For experimental / research use only.
Taraxerol 98%
BOC Sciences
For experimental / research use only.
Taraxerol
Coompo
For experimental / research use only.
Taraxerol from Plants ≥96%
Sigma-Aldrich
For experimental / research use only.
3β-Taraxerol

Safety Information:

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 taraxerol usage levels up to:
not for fragrance use.
Recommendation for taraxerol 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 :92097
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(3S,4aR,6aR,6aS,8aR,12aR,14aR,14bR)-4,4,6a,6a,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,8,9,10,12,12a,13,14,14a-tetradecahydropicen-3-ol
Chemidplus:0000127220

References:

(3S,4aR,6aR,6aS,8aR,12aR,14aR,14bR)-4,4,6a,6a,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,8,9,10,12,12a,13,14,14a-tetradecahydropicen-3-ol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):92097
Pubchem (sid):135047910

Other Information:

(IUPAC):Atomic Weights of the Elements 2011 (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
KEGG (GenomeNet):C08637
HMDB (The Human Metabolome Database):HMDB34920
FooDB:FDB013505
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

Potential Blenders and core components :

None Found

Potential Uses:

None Found

Occurrence (nature, food, other):

basswood bark
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cantaloupe seed
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cucumber seed
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dandelion plant
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dandelion root
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diospyros spp.
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grape leaf
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grape stem
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hazelnut leaf
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linden little-leaf linden
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melon bitter melon seed oil
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persimmon
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shea tree seed oil
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soybean seed
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tea seed oil
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Synonyms:

alnulin
(3beta)-dextro-friedoolean-14-en-3-ol
D-friedoolean-14-en-3b-ol
dextro-friedoolean-14-en-3beta-ol
(3S,4aR,6aR,6aS,8aR,12aR,14aR,14bR)-4,4,6a,6a,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,8,9,10,12,12a,13,14,14a-tetradecahydropicen-3-ol
isoolean-14-en-3b-ol
skimmiol
tiliadin

Articles:

PubMed:Pereskia aculeata miller leaves present in vivo topical anti-inflammatory activity in models of acute and chronic dermatitis.
PubMed:Effects of Lupenone, Lupeol, and Taraxerol Derived from Adenophora triphylla on the Gene Expression and Production of Airway MUC5AC Mucin.
PubMed:Hydrogen isotope response to changing salinity and rainfall in Australian mangroves.
PubMed:Occurrence of taraxerol and taraxasterol in medicinal plants.
PubMed:Antinociceptive and anti-inflammatory activities of Schefflera octophylla extracts.
PubMed:Cardanols, long chain cyclohexenones and cyclohexenols from Lannea schimperi (Anacardiaceae).
PubMed:[Chemical constituents of Clerodendrum trichotomum Leaves].
PubMed:Distribution and sources of lipid compound series in sediment cores of the southern South China Sea.
PubMed:Abroma augusta L. (Malvaceae) leaf extract attenuates diabetes induced nephropathy and cardiomyopathy via inhibition of oxidative stress and inflammatory response.
PubMed:Effects of single, binary and tertiary combinations with Jatropha gossypifolia and other plant-derived molluscicides on reproduction and survival of the snail Lymnaea acuminata.
PubMed:[Study on chemical constituents from leaf of Bombax ceiba (II)].
PubMed:A new triterpenoid from Sapium baccatum (Euphorbiaceae).
PubMed:Cholinesterase inhibitory triterpenoids from the bark of Garcinia hombroniana.
PubMed:A new cinnamoylglycoflavonoid, antimycobacterial and antioxidant constituents from Heritiera littoralis leaf extracts.
PubMed:Interactions of antiparasitic sterols with sterol 14α-demethylase (CYP51) of human pathogens.
PubMed:Triterpenes from Euphorbia hirta and their cytotoxicity.
PubMed:A new taraxerol derivative from the roots of Microcos tomentosa.
PubMed:Anti-plasmodial activity of some Zulu medicinal plants and of some triterpenes isolated from them.
PubMed:Antimicrobial activity and cytotoxicity of triterpenes isolated from leaves of Maytenus undata (Celastraceae).
PubMed:[Study on chemical constituents of root bark of Discocleidion rufescens].
PubMed:Taraxerol inhibits LPS-induced inflammatory responses through suppression of TAK1 and Akt activation.
PubMed:New sesquiterpenes and phenolic compound from Ficus foveolata.
PubMed:Reversal of dexamethasone induced insulin resistance in 3T3L1 adipocytes by 3β-taraxerol of Mangifera indica.
PubMed:Standardized Clitoria ternatea leaf extract as hyaluronidase, elastase and matrix-metalloproteinase-1 inhibitor.
PubMed:Production of triterpenoid anti-cancer compound taraxerol in Agrobacterium-transformed root cultures of butterfly pea (Clitoria ternatea L.).
PubMed:Source correlation of biomarkers in a mangrove ecosystem on Santa Catarina Island in southern Brazil.
PubMed:Impact of Taraxerol in combination with extract of Euphorbia tirucalli plant on biological parameters of Lymnaea acuminata.
PubMed:Effect of bioactive compounds extracted from euphorbious plants on hematological and biochemical parameters of Channa punctatus.
PubMed:[Studies on the chemical constituents of Codonopsis pilosula].
PubMed:[Effects of taraxerol and taraxerol acetate on cell cycle and apoptosis of human gastric epithelial cell line AGS].
PubMed:Antiparasitic compounds from Cupania cinerea with activities against Plasmodium falciparum and Trypanosoma brucei rhodesiense.
PubMed:Anti-inflammatory diterpene from Thyrsanthera suborbicularis.
PubMed:Antiproliferative constituents of the roots of Conyza canadensis.
PubMed:[Studies on the triterpenoids of Vitex trifolia].
PubMed:[Chemical constituents of Discocleidion rufescens].
PubMed:Determination of the phenolic content and antioxidant potential of crude extracts and isolated compounds from leaves of Cordia multispicata and Tournefortia bicolor.
PubMed:Cloning and characterization of oxidosqualene cyclases from Kalanchoe daigremontiana: enzymes catalyzing up to 10 rearrangement steps yielding friedelin and other triterpenoids.
PubMed:Triterpenoids from the roots of Pterospermum heterophyllum Hance.
PubMed:[Terpenoids from Euphorbia antiquorum L.].
PubMed:[Studies on the chemical constituents from Euphorbia chrysocoma].
PubMed:3beta-taraxerol of Mangifera indica, a PI3K dependent dual activator of glucose transport and glycogen synthesis in 3T3-L1 adipocytes.
PubMed:Antimicrobial and cytotoxic constituents from leaves of Sapium baccatum.
PubMed:[Study on the chemical constituents of Uvaria microcarpa].
PubMed:Active compounds against tinea pedis dermatophytes from Ageratina pichinchensis var. bustamenta.
PubMed:Antifungal activity of Eugenia umbelliflora against dermatophytes.
PubMed:Phytochemical analyses and gastroprotective effects of Eugenia umbelliflora (Myrtaceae) on experimental gastric ulcers.
PubMed:Isolation and characterization of xanthine oxidase inhibitory constituents of Pyrenacantha staudtii.
PubMed:Antiproliferative compounds of Helmiopsis sphaerocarpa from the Madagascar rainforest.
PubMed:[Studies on chemical constituents of root tuber of cultivated Pseudostellaria heterophylla (Zheshen No. 1)].
PubMed:[Studies on chemical constituents from roots of Pterospermum heterophyllum].
PubMed:[Chemical constituents in the leave of Rhizophora stylosa L and their biological activities].
PubMed:Photochemical alteration of 3-oxygenated triterpenoids: implications for the origin of 3,4-seco-triterpenoids in sediments.
PubMed:New diterpenoids and the bioactivity of Erythrophleum fordii.
PubMed:A new cytotoxic prenylated dihydrobenzofuran derivative and other chemical constituents from the rhizomes of Atractylodes lancea DC.
PubMed:Triterpenoids and a sterol from the stem-bark of Styrax japonica and their protein tyrosine phosphatase 1B inhibitory activities.
PubMed:[Studies on chemical constituents from whole plants of Crossostephium chinense].
PubMed:Pentacyclic triterpenoids from the mangrove plant Rhizophora stylosa.
PubMed:[Triterpenoids and steroids from Excoecaria agallocha].
PubMed:Validation of HPTLC method for the analysis of taraxerol in Clitoria ternatea.
PubMed:Lipid biomarkers in suspended particles from a subtropical estuary: assessment of seasonal changes in sources and transport of organic matter.
PubMed:Triterpene synthases from the Okinawan mangrove tribe, Rhizophoraceae.
PubMed:[Studies on the chemical constituents of Vaccinium iteophyllum].
PubMed:Chemical constituents from the roots of Homonoia riparia.
PubMed:Identification and determination of triterpenoids in Hieracium pilosella L.
PubMed:Pentacyclic triterpenes with selective bioactivity from Sebastiania adenophora leaves, Euphorbiaceae.
PubMed:Two novel C29-5beta-sterols from the stems of Opuntia dillenii.
PubMed:[Study on the chemical constituents of Mitragyna rotundifolia].
PubMed:Oleanane-type triterpenes of Embelia schimperi leaves.
PubMed:Two new 18-en-oleane derivatives from marine mangrove plant, Barringtonia racemosa.
PubMed:Natural product biomarkers as indicators of sources and transport of sedimentary organic matter in a subtropical river.
PubMed:The chemical constituents of Rhododendron ovatum Planch.
PubMed:New furofuran and butyrolactone lignans with antioxidant activity from the stem bark of Styrax japonica.
PubMed:[Studies on chemical constituents of Clerodendrum bungei].
PubMed:A new triterpenoid: taraxerol-3-beta-O-tridecyl ether from Derris triofoliata.
PubMed:Studies on the chemical constituents of the roots of Rhododendron molle G. Don.
PubMed:New cytotoxic terpenoids from the wood of Vepris punctata from the Madagascar Rainforest.
PubMed:Pentacyclic triterpenoid esters from the fruits of Bruguiera cylindrica.
PubMed:Acetylcholinesterase inhibitors from the twigs of Vaccinium oldhami Miquel.
PubMed:Taraxer-14-en-3beta-ol, an anti-inflammatory compound from Sterculia foetida L.
PubMed:Potential cancer chemopreventive constituents of the leaves of Macaranga triloba.
PubMed:[Studies on chemical constituents of Uvaria macrophylia].
PubMed:[A study on chemical components of Tetrastigma hemsleyanum Diels et Gilg. Native to China].
PubMed:Anti-inflammatory and antimicrobial activities of triterpenoids from Strobilanthes callosus nees.
PubMed:Cytotoxic principles from Ventilago leiocarpa.
PubMed:A phytochemical investigation of Alchornea latifolia.
PubMed:Taraxerol acetate at 100 K.
PubMed:Rhizophora mangle (Rhizophoraceae) triterpenoids with insecticidal activity.
PubMed:Anti-carcinogenic activity of Taraxacum plant. II.
PubMed:Distribution of pyranocoumarins in Calophyllum cordato-oblongum.
PubMed:Triterpene alcohols from the flowers of compositae and their anti-inflammatory effects.
PubMed:[Chemical components of Codonopsis pilosula (Franch.) Nannf. var. volubilis (Nannf.) L.T. Shen].
PubMed:[Chemical constituents in the leaves of Mangifera persiciformis C.Y. Wu et Y.L. Ming].
PubMed:[Chemical constituents of Sageretia theezans Brongn].
PubMed:Antibacterial, antifungal and anthelmintic activities of root barks of Uvaria hookeri and Uvaria narum.
PubMed:[Chemical constituents of the leaves of Acanthopanax trifoliatus (Linn) Merr].
PubMed:Isolation of myricadiol, myricitrin, taraxerol, and taraxerone from Myrica cerifera L. root bark.
PubMed:[Studies on the neutral constituents of Pachysandra terminalis Sieb. et Zucc. II. Identification of taraxerol and isolation of compound-3A and 3B].
PubMed:[Studies on the constituents of Acanthopanax sciadophylloides Franch. et Sav. 3. Higher fatty acid esters of taraxerol].
PubMed:Taraxerol from Careya arborea.
PubMed:The isolation of taraxerol, taraxeryl acetate, and taraxerone from Crossostephium chinense Makino (Compositae).
PubMed:TARAXEROL FROM CLITORIA TERNATEA LINN.
PubMed:A new source of taraxerol.
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