Page last updated: 2024-12-11

triolein

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Occurs in Manufacturing Related Drugs Related Conditions Protein Interactions Research Growth

Description

Triolein: (Z)-9-Octadecenoic acid 1,2,3-propanetriyl ester. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

triolein : A triglyceride formed by esterification of the three hydroxy groups of glycerol with oleic acid. Triolein is one of the two components of Lorenzo's oil. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID5497163
CHEMBL ID4297656
CHEBI ID53753
SCHEMBL ID23730
MeSH IDM0022006

Synonyms (110)

Synonym
trioleyl glycerol
trioleate, glycerol
trioleate-glycerin
glycerol, trioleyl
trioleate glycerin
LMGL03010250
tg(18:1(9z)/18:1(9z)/18:1(9z))
1,2,3-tri-oleoyl-glycerol
1,2,3-tri-(9z-octadecenoyl)-glycerol
propane-1,2,3-triyl (9z,9'z,9''z)tris-octadec-9-enoate
einecs 204-534-7
raoline
1,2,3-propanetriyl trioleate
estol 1433
glyceryl-1,2,3-trioleate
hsdb 5594
oleic acid triglyceride
glyceryl trioleate
trioleoylglyceride
emerest 2423
kaolube 190
kemester 1000
oleyl triglyceride
edenor nhti-g
actor lo 1
9-octadecenoic acid (9z)-, 1,2,3-propanetriyl ester
1,2,3-propanetriol tri(9-octandecenoate)
oleic triglyceride
emery 2423
triolein
olein
olein, tri-
1,2,3-tri(cis-9-octadecenoyl)glycerol
triolein, [9,10-3h(n)]-
9-octadecenoic acid, 1,2,3-propanetriyl ester
triglyceride ooo
glycerol triolein
sn-glyceryl trioleate
glycerin trioleate
emery oleic acid ester 2230
122-32-7
9-octadecenoic-9,10-t2 acid, 1,2,3-propanetriyl ester, (z,z,z)- (9ci)
9-octadecenoic acid, 1,2,3-propanetriyl ester, (9z,9'z,9''z)-
9-octadecenoic acid (z)-, 1,2,3-propanetriyl ester
glycerol trioleate
radia 7363
trioleoylglycerol
aldo to
glycerol, tri(cis-9-octadecenoate)
glyceryl trioleate, ~65%
glyceryl trioleate, >=99%
triolein c18:1
glyceryl trioleate, >=97.0% (tlc)
AC7B54B8-0E34-455F-A1E0-442F3ECD69EA
2,3-bis[[(z)-octadec-9-enoyl]oxy]propyl (z)-octadec-9-enoate
propane-1,2,3-triyl tris[(9z)-octadec-9-enoate]
(z)-9-octadecenoic acid, 1,2,3-propanetriyl ester
CHEBI:53753 ,
tg(18:1(9z)/18:1(9z)/18:1(9z))[iso]
G0089
ec 204-534-7
o05ec62663 ,
9-octadecenoic acid (9z)-, 1,1',1''-(1,2,3-propanetriyl) ester
unii-o05ec62663
ccris 8687
S3590
(9z)9-octadecenoic acid 1,2,3-propanetriyl ester
EPITOPE ID:117714
1,2,3-propanetriyl ester
tri(cis-9-octadecenoate)
glyceryl trioleate [ii]
glyceryl trioleate [hsdb]
triolein [mi]
glyceryl trioleate [vandf]
triolein [inci]
triolein [who-dd]
glyceryl trioleate [who-dd]
triolein [usp-rs]
glyceryl trioleate [mart.]
SCHEMBL23730
PHYFQTYBJUILEZ-IUPFWZBJSA-N
AKOS024437536
mfcd00137563
DTXSID3026988 ,
J-004788
glyceryl trioleate, technical, >=60% (gc)
glyceryl trioleate, analytical reference material
(z)-1,2,3-propanetriyl ester 9-octadecenoic acid
1,2,3-tri-(9z-octadecenoyl)-sn-glycerol
(z)-1,2,3-propanetriyl ester 9-octadecenoate
(9z)-1,1',1''-(1,2,3-propanetriyl) ester 9-octadecenoate
(9z)-1,1',1''-(1,2,3-propanetriyl) ester 9-octadecenoic acid
(9z)-1,2,3-propanetriyl ester 9-octadecenoate
(9z)-1,2,3-propanetriyl ester 9-octadecenoic acid
triolein, european pharmacopoeia (ep) reference standard
tg 54:3
triolein, tech grade
DB13038
HY-N1981
Q413929
tri-olein
CS-0018302
1,3-bis[(9z)-octadec-9-enoyloxy]propan-2-yl (9z)-octadec-9-enoate
CHEMBL4297656
glyceryltrioleate
glyceryl trioleate (ii)
glyceryl trioleate (mart.)
triolein (usp-rs)
dtxcid006988
propane-1,2,3-triyl tris((9z)-octadec-9-enoate)

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Trilinolenin (18:3; omega-3) was toxic only after prolonged incubation."( Toxicity of polyunsaturated fatty acid esters for human monocyte-macrophages: the anomalous behaviour of cholesteryl linolenate.
Carpenter, KL; Hardwick, SJ; Hird, R; Law, NS; Marchant, CE; Mitchinson, MJ; Van Der Veen, C, 1997
)
0.3
" Adverse events (AEs) were recorded throughout the 12-week trial."( The safety of the use of ethyl oleate in food is supported by metabolism data in rats and clinical safety data in humans.
Balm, TK; Bharaj, SS; Bookstaff, RC; Kelm, GR; Kulick, RM; Murray, JV; PaiBir, S, 2003
)
0.32
" On the basis of the bioavailability model, it was estimated that approximately 17-22% and 13-18% of BkF-HA complex contributed to the bioaccumulation and/or to the induced toxic effect, correspondingly."( Influence of humic acid on bioavailability and toxicity of benzo[k]fluoranthene to Japanese medaka.
Chen, S; Ke, R; Khan, SU; Wang, Z; Zha, J, 2008
)
0.35
" Combining systemic EA with intrathecal DOX-chemotherapy via Ommaya reservoirs may reduce DOX concentrations in systemic circulation, hinder toxic interactions with EA and induce selective kill of glioma cells."( Erucic acid, a component of Lorenzo's oil and PPAR-δ ligand modifies C6 glioma growth and toxicity of doxorubicin. Experimental data and a comprehensive literature analysis.
Altinoz, MA; Bilir, A; Elmaci, İ, 2018
)
0.48

Pharmacokinetics

ExcerptReferenceRelevance
" The pharmacokinetics following intramuscular injection of the multivesicular liposome of thymopentin labeled with fluorescein isothiocyanate in rats showed that the peak concentration of thymopentin was lower and elimination of it was slower significantly than that of thymopentin labeled with fluorescein isothiocyanate solution in the same dose."( [Preparation of sustained release multivesicular liposome for thymopentin and preliminary study on its pharmacokinetics in rats].
Jiao, YH; Mu, HJ; Sun, KX; Wang, T; Yao, DG; Yuan, ZZ, 2008
)
0.35

Compound-Compound Interactions

ExcerptReferenceRelevance
"High-purity trilinolein and triolein were prepared by Novozym 435-catalyzed esterification reaction combined with column chromatography purification in this study."( Preparation of High-Purity Trilinolein and Triolein by Enzymatic Esterification Reaction Combined with Column Chromatography.
Chen, Z; Lan, T; Li, H; Pan, L; Wu, D; Zhao, B, 2019
)
0.51

Bioavailability

Triolein-embedded cellulose acetate membrane (TECAM) was buried in 15 field-contaminated soils in parallel with the cultivation of wheat to predict bioavailability of naphthalene, phenanthrene, pyrene, and benzo[a]pyrene to wheat roots. The method was compared with chemical extraction methods.

ExcerptReferenceRelevance
"The intestinal absorption rate of dissolved griseofulvin was determined from: (a) an aqueous phase, (b) an aqueous phase containing a micellar phase composed of taurodeoxycholate, monoolein, and oleic acid, and (c) an aqueous phase containing the micellar phase and emulsified triolein."( Intestinal absorption of griseofulvin from a triolein digestion mixture in rats.
Grisafe, JA; Hayton, WL, 1978
)
0.26
"To determine the extent to which suckling animals differ from adults in their capacity to absorb fat, we compared the rate of absorption of orally administered [14C]triolein in 11- to 12-day-old suckling rats with that of 10-wk-old adults by three distinct methods."( Rates of triolein absorption in suckling and adult rats.
Flores, CA; Hing, SA; Koldovský, O; Wells, MA, 1989
)
0.28
" Intravenous somatostatin did not alter gastric motility or the rate of absorption of the labeled glucose; lipid absorption, however, was markedly impaired."( Influence of somatostatin on gastric motility and meal absorption in rhesus monkeys, Macaca mulatta.
Hansen, BC; Koerker, DJ, 1981
)
0.26
" They further our understanding of the bioavailability of polar and apolar carotenoids and of their distribution between lipoprotein particles."( Carotenoids in biological emulsions: solubility, surface-to-core distribution, and release from lipid droplets.
Armand, M; Azais-Braesco, V; Borel, P; Grolier, P; Lafont, H; Lairon, D; Partier, A, 1996
)
0.29
" Both test materials were well absorbed with approximately 70-90% of the EO dose absorbed and approximately 90-100% of the TG dose absorbed."( The safety of the use of ethyl oleate in food is supported by metabolism data in rats and clinical safety data in humans.
Balm, TK; Bharaj, SS; Bookstaff, RC; Kelm, GR; Kulick, RM; Murray, JV; PaiBir, S, 2003
)
0.32
" This paper describes a method for extracting organic chemicals from sediments and then re-introducing them into water column toxicity tests in a way that mimics, at least in part, the partitioning processes that govern bioavailability in sediment."( Method for testing the aquatic toxicity of sediment extracts for use in identifying organic toxicants in sediments.
Heinis, LJ; Highland, TL; Mount, DR, 2004
)
0.32
" The absorption rate for lipophilic pollutants was very fast and exhibited some relationship with the octanol--water partition coefficient of the analyte."( A biomimetic absorbent for removal of trace level persistent organic pollutants from water.
Dai, R; Liu, H; Qu, J; Ru, J; Wang, Z, 2007
)
0.34
" The data indicate that TECAM represents a useful surrogate to estimate the bioavailability of PAHs and perhaps other hydrophobic organic contaminants (HOCs) in soils."( Biomimetic accumulation of PAHs from soils by triolein-embedded cellulose acetate membranes (TECAMs) to estimate their bioavailability.
Christie, P; Ke, R; Shan, XQ; Tao, Y; Wang, Z; Zhang, S, 2008
)
0.35
"Adsorption to dissolved organic matter (DOM) may significantly decrease the freely dissolved concentration of many hydrophobic organic compounds and, hence, result in reduced bioavailability to aquatic organisms."( Predicting bioavailability and accumulation of organochlorine pesticides by Japanese medaka in the presence of humic acid and natural organic matter using passive sampling membranes.
Ke, R; Luo, J; Spear, PA; Sun, L; Wang, Z, 2007
)
0.34
" To compare the relative effects of co-administration of P-gp/CYP modulators on intestinal lymphatic transport versus systemic bioavailability of saquinavir."( An examination of the effect of intestinal first pass extraction on intestinal lymphatic transport of saquinavir in the rat.
Griffin, BT; O'Driscoll, CM, 2008
)
0.35
" A comparison of the relative enhancement of lymphatic transport and plasma bioavailability compared to control (i."( An examination of the effect of intestinal first pass extraction on intestinal lymphatic transport of saquinavir in the rat.
Griffin, BT; O'Driscoll, CM, 2008
)
0.35
" These results suggest that exfoliated colonic epithelial cells isolated from stool samples of human subjects can be maintained in culture and serve as a useful non-invasive system to study the bioavailability of vitamin A and provitamin A carotenoids."( In vitro uptake of β-carotene by human exfoliated colonic epithelial cells.
Gireesh, T; Sudhakaran, PR, 2009
)
0.35
"Triolein-embedded cellulose acetate membrane (TECAM) was buried in 15 field-contaminated soils in parallel with the cultivation of wheat to predict bioavailability of naphthalene, phenanthrene, pyrene, and benzo[a]pyrene to wheat roots, and the method was compared with chemical extraction methods."( Predicting bioavailability of PAHs in soils to wheat roots with triolein-embedded cellulose acetate membranes and comparison with chemical extraction.
Christie, P; Tao, Y; Wang, Z; Zhang, S, 2008
)
0.35
" These results suggest that TECAM can be a useful tool to predict bioavailability of PAHs in field-contaminated soils."( Predicting bioavailability of PAHs in field-contaminated soils by passive sampling with triolein embedded cellulose acetate membranes.
Christie, P; Tao, Y; Wang, Z; Zhang, S, 2009
)
0.35
"95 confidence band of HA-free control thereby indicating the participation of BkF-HA complex to the bioavailability and toxicity."( Influence of humic acid on bioavailability and toxicity of benzo[k]fluoranthene to Japanese medaka.
Chen, S; Ke, R; Khan, SU; Wang, Z; Zha, J, 2008
)
0.35
" In general, this research provides important information about the factors influencing the bioaccessibility of emulsified vitamin E, which could be used to design more effective emulsion-based delivery systems for increasing the oral bioavailability of this important bioactive component."( Enhancing vitamin E bioaccessibility: factors impacting solubilization and hydrolysis of α-tocopherol acetate encapsulated in emulsion-based delivery systems.
Decker, EA; McClements, DJ; Xiao, H; Yang, Y, 2015
)
0.42
" Previous studies have shown that natural sesame oil promotes the intestinal lymphatic transport and oral bioavailability of the highly lipophilic drug cannabidiol (CBD)."( Natural sesame oil is superior to pre-digested lipid formulations and purified triglycerides in promoting the intestinal lymphatic transport and systemic bioavailability of cannabidiol.
Barrett, DA; Berton, M; Bettonte, S; Chu, Y; Constantinescu, CS; Feng, W; Fischer, PM; Gershkovich, P; Lee, JB; Qin, C; Stocks, MJ; Zgair, A, 2021
)
0.62

Dosage Studied

Triolein marked with 13C and processed in soybean oil is administered intravenously at a dosage of 10 mg/kg. The fractional absorption of 14C-triolein was calculated from the average ratios of14C/51Cr dosed and measured in the feces.

ExcerptRelevanceReference
" The hourly 14CO2 production was measured for 12 h for estimating the oxidation rate of dosed triacylglycerols."( Limits of medium-chain and long-chain triacylglycerol utilization by neonatal piglets.
Chiang, SH; Clarke, SD; Cornelius, SG; Pettigrew, JE, 1990
)
0.28
" Triolein marked with 13C and processed in soybean oil is administered intravenously at a dosage of 10 mg/kg."( [Fat utilization in newborn infants with and without heparin administration. Comparative study with the 13C-triolein breath test].
Brösicke, H; Helge, H; Knoblach, G; Park, W; Paust, H, 1985
)
0.27
" After administration of an oral dose of labeled cholesterol ((14)C or (3)H) and an intravenous dose of colloidal labeled cholesterol ((3)H or (14)C) the ratio of the two labels in plasma or whole blood 48 hr or more after dosing compared closely to the ratio of areas under the respective specific activity-time curves."( Validation of a dual-isotope plasma ratio method for measurement of cholesterol absorption in rats.
Hughes, LB; Zilversmit, DB, 1974
)
0.25
" The fractional absorption of 14C-triolein was calculated from the average ratios of 14C/51Cr dosed and measured in the feces."( Olestra ingestion and dietary fat absorption in humans.
Cooper, DA; Daher, GC; King, D; Peters, JC; Riccardi, KA; Zorich, NL, 1997
)
0.3
"A cremophor mixed micelle formulation of saquinavir alone, or co-administered with P-gp/CYP modulators, verapamil, ketoconazole or cyclosporine, was dosed intraduodenally in the mesenteric lymph duct cannulated anaesthetized rat model."( An examination of the effect of intestinal first pass extraction on intestinal lymphatic transport of saquinavir in the rat.
Griffin, BT; O'Driscoll, CM, 2008
)
0.35
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Occurs in Manufacturing (1 Product(s))

Product Categories

Product CategoryProducts
Beauty & Personal Care1

Products

ProductBrandCategoryCompounds Matched from IngredientsDate Retrieved
Alba Botanica Hawaiian Detox Sheet Mask Volcanic Clay -- 1 MaskAlbaBeauty & Personal Careorange, citric acid, allantoin, allyl caproate, betaine, citric acid, tocopherol, triethyl citrate, ethylhexylglycerin, tocopherol, glycerin, linoleic acid, glyceryl caprylate, oleic acid, palmitic acid, palmitic acid, phenoxyethanol, potassium hydroxide, sodium benzoate, stearic acid, triolein2024-11-29 10:47:42

Roles (2)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Caenorhabditis elegans metaboliteA nematode metabolite produced by Caenorhabditis elegans.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
triglycerideAny glyceride resulting from the condensation of all three hydroxy groups of glycerol (propane-1,2,3-triol) with fatty acids.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (2)

PathwayProteinsCompounds
Triacylglycerol Degradation TG(18:1(9Z)/18:1(9Z)/18:1(9Z))511
De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:1(9Z))513

Research

Studies (1,626)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990924 (56.83)18.7374
1990's271 (16.67)18.2507
2000's246 (15.13)29.6817
2010's165 (10.15)24.3611
2020's20 (1.23)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials36 (2.13%)5.53%
Reviews44 (2.60%)6.00%
Case Studies34 (2.01%)4.05%
Observational0 (0.00%)0.25%
Other1,578 (93.26%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]