Compounds > diisopropanolamine
Page last updated: 2024-12-05

diisopropanolamine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Diisopropanolamine (DIPA) is a colorless, viscous liquid with a faint amine odor. It is a tertiary amine, meaning that the nitrogen atom is bonded to three alkyl groups. DIPA is a versatile chemical used in various industries, primarily as an emulsifier, surfactant, and corrosion inhibitor. DIPA is produced through the reaction of propylene oxide with ammonia in a multi-step process. The synthesis involves several steps including: 1) the reaction of propylene oxide with ammonia to form monoisopropanolamine (MIPA), 2) the reaction of MIPA with propylene oxide to form diisopropanolamine (DIPA), and 3) the reaction of DIPA with propylene oxide to form triisopropanolamine (TIPA). The reaction conditions, such as temperature, pressure, and catalyst, play a crucial role in controlling the selectivity and yield of the desired product. DIPA is used in various industries, including: 1) Cosmetics: as an emulsifier and thickener in shampoos, conditioners, and creams, 2) Pharmaceuticals: as an intermediate in the synthesis of various pharmaceuticals, 3) Agriculture: as a component in pesticide formulations, 4) Metalworking: as a corrosion inhibitor and lubricant, and 5) Oil and gas: as an emulsifier and corrosion inhibitor in drilling fluids. DIPA is also studied for its potential applications in various areas, including: 1) Carbon dioxide capture: due to its ability to absorb carbon dioxide, DIPA is being investigated as a potential absorbent for carbon capture and storage technologies, 2) Biofuel production: DIPA is being studied as a potential catalyst for the production of biodiesel from vegetable oils, and 3) Nanotechnology: DIPA is being explored as a component in the synthesis of nanomaterials. The potential environmental and health effects of DIPA have been studied. DIPA is considered to be a relatively safe chemical for industrial use. However, it can be irritating to the skin, eyes, and respiratory system. DIPA is a valuable chemical used in various industries. Its versatility and effectiveness make it a key component in many products and processes. The ongoing research on DIPA focuses on exploring new applications and optimizing its use for sustainable development.'

diisopropanolamine: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

diisopropanolamine : A secondary amino compound that is diethanolamine substituted by methyl groups at positions 1 and 1'. It is a versatile chemical used in a variety of personal care, cosmetic and industrial products. [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 CID8086
CHEMBL ID2106303
CHEBI ID143266
SCHEMBL ID22774
MeSH IDM0166907

Synonyms (80)

Synonym
nsc4963
dipropyl-2,2'-dihydroxy-amine
1,1'-iminodi-2-propanol
2-propanol,1'-iminobis-
wln: qy1 & 1m1yq1
110-97-4
2-propanol,1'-iminodi-
bis(2-propanol)amine
diisopropanolamine
bis(2-hydroxypropyl)amine
nsc-4963
1,1'-iminobis[2-propanol]
1,1'-iminodipropan-2-ol
2-propanol, 1,1'-iminobis-
nsc 4963
2-propanol, 1,1'-iminodi-
hsdb 338
dipa (alcohol)
ccris 6234
einecs 203-820-9
di-2-propanolamine
brn 0605363
n,n-bis(2-hydroxypropyl)amine
1,1'-iminobis-2-propanol
1-[(2-hydroxypropyl)amino]propan-2-ol
STK503623
bis(2-hydroxypropyl)amine, >=98.0% (t)
9AFD2C98-2177-4499-8EB2-1C8EA079F21D
D0924
1-(2-hydroxypropylamino)propan-2-ol
CHEBI:143266
dipa alcohol
1,1'-azanediyldi(propan-2-ol)
di(2-hydroxypropyl)amine
1,1'-azanediylbis propan-2-ol
AKOS005457854
NCGC00249081-01
dtxsid8020179 ,
tox21_302859
cas-110-97-4
NCGC00256476-01
dtxcid20179
tox21_201602
NCGC00259151-01
BBL013266
68153-96-8
di-isopropanolamine
CHEMBL2106303
3-04-00-00761 (beilstein handbook reference)
unii-0w44hyl8t5
0w44hyl8t5 ,
ec 203-820-9
diisopropanolamine [ii]
diisopropanolamine [inci]
diisopropanolamine [hsdb]
1,1'-iminobis(2-propanol)
diisopropanolamine [mi]
diisopropanolamine [vandf]
diisopropanolamine [mart.]
diisopropanol amine
di-isopropanol amine
bis-(2-hydroxypropyl)-amine
diiso-propanolamine
SCHEMBL22774
1,1'-azanediylbis(propan-2-ol)
J-660021
dipa low freeze grade 85 (salt/mix)
dipa low freeze grade 90 (salt/mix)
1,1'-imino-di(2-propanol)
di(2-hydroxy-n-propyl) amine
F0001-0230
mfcd00004531
bis-(2-hydroxypropyl)amine
1335-54-2
1,1'-azanediyldipropan-2-ol
VS-03726
Q777543
AMY25531
diisopropanolamin
EN300-722418

Research Excerpts

Overview

Diisopropanolamine is a "sweetening agent" used to remove hydrogen sulfide from sour natural gas. It is a contaminant at some sour gas treatment facilities in western Canada.

ExcerptReferenceRelevance
"Diisopropanolamine (DIPA) is a "sweetening agent" used to remove hydrogen sulfide from sour natural gas, and it is a contaminant at some sour gas treatment facilities in western Canada. "( Microbial mineralization of diisopropanolamine.
Coy, DL; Fedorak, PM; Gieg, LM, 1999)		2.04

Toxicity

ExcerptReferenceRelevance
" Fischer 344/DuCrl rats were given up to 750 mg/kg/day by dermal application, 5 days/week, for 4 weeks; or up to 1,000 mg DIPA/kg/day by drinking water for 13 weeks to evaluate potential toxic effects."( Repeated dose toxicity and developmental toxicity of diisopropanolamine to rats.
Brooks, KJ; Carney, EW; Dryzga, MD; Johnson, KA; Stott, WT; Tornesi, B, 2007)		0.59
" In the present study, safe and effective ionic liquids for transdermal absorption were obtained as salts generated by a neutralization reaction between highly biocompatible aliphatic carboxylic acids (octanoic acid or isostearic acid) and aliphatic amines (diisopropanolamine or triisopropanolamine) (Medrx Co."( The molecular assembly of the ionic liquid/aliphatic carboxylic acid/aliphatic amine as effective and safety transdermal permeation enhancers.
Kubota, K; Shibata, A; Yamaguchi, T, 2016)		0.61

Bioavailability

ExcerptReferenceRelevance
"This study was conducted to determine the relative dermal bioavailability (absorption), distribution, metabolism, and excretion (ADME) of diisopropanolamine (DIPA), an alcohol amine used in a number of industrial and personal care products."( Pharmacokinetics and bioavailability of diisopropanolamine (DIPA) in rats following intravenous or dermal application.
Bartels, MJ; Frantz, SW; Lowe, ER; Nolan, RJ; Rick, DL; Saghir, SA; Spence, MW, 2007)		0.81
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
surfactantA substance which lowers the surface tension of the medium in which it is dissolved, and/or the interfacial tension with other phases, and, accordingly, is positively adsorbed at the liquid/vapour and/or at other interfaces.
emulsifierThe chemical role played by a substance that stabilizes an emulsion by increasing its kinetic stability.
bufferAny substance or mixture of substances that, in solution (typically aqueous), resists change in pH upon addition of small amounts of acid or base.
[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 (3)

ClassDescription
secondary amino compoundA compound formally derived from ammonia by replacing two hydrogen atoms by organyl groups.
secondary alcoholA secondary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has two other carbon atoms attached to it.
aminodiolAn amino alcohol having two hydroxy functional groups.
[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]

Protein Targets (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
GLI family zinc finger 3Homo sapiens (human)Potency0.61130.000714.592883.7951AID1259369
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency69.00830.003041.611522,387.1992AID1159552
pregnane X nuclear receptorHomo sapiens (human)Potency61.50380.005428.02631,258.9301AID1346982
aryl hydrocarbon receptorHomo sapiens (human)Potency35.50700.000723.06741,258.9301AID743085; AID743122
Histone H2A.xCricetulus griseus (Chinese hamster)Potency50.47720.039147.5451146.8240AID1224845
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency61.50380.000627.21521,122.0200AID743202; AID743219
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (27.27)18.7374
1990's2 (18.18)18.2507
2000's5 (45.45)29.6817
2010's1 (9.09)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 47.00

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index47.00 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.50 (4.65)
Search Engine Demand Index66.85 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (47.00)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies3 (27.27%)4.05%
Observational0 (0.00%)0.25%
Other8 (72.73%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
choline
[no description available]		7.0410cholinesallergen;
Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
neurotransmitter;
nutrient;
plant metabolite;
Saccharomyces cerevisiae metabolite
octanoic acid
octanoic acid: RN given refers to parent cpd; structure in Merck Index, 9th ed, #1764. octanoic acid : A straight-chain saturated fatty acid that is heptane in which one of the hydrogens of a terminal methyl group has been replaced by a carboxy group. Octanoic acid is also known as caprylic acid.		2.1310medium-chain fatty acid;
straight-chain saturated fatty acid		antibacterial agent;
Escherichia coli metabolite;
human metabolite
nitrates
Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.		210monovalent inorganic anion;
nitrogen oxoanion;
reactive nitrogen species
nitrites
Nitrites: Salts of nitrous acid or compounds containing the group NO2-. The inorganic nitrites of the type MNO2 (where M=metal) are all insoluble, except the alkali nitrites. The organic nitrites may be isomeric, but not identical with the corresponding nitro compounds. (Grant & Hackh's Chemical Dictionary, 5th ed)		1.9710monovalent inorganic anion;
nitrogen oxoanion;
reactive nitrogen species		human metabolite
phenolsulfonphthalein
Phenolsulfonphthalein: Red dye, pH indicator, and diagnostic aid for determination of renal function. It is used also for studies of the gastrointestinal and other systems.. phenol red : 3H-2,1-Benzoxathiole 1,1-dioxide in which both of the hydrogens at position 3 have been substituted by 4-hydroxyphenyl groups. A pH indicator changing colour from yellow below pH 6.8 to bright pink above pH 8.2, it is commonly used as an indicator in cell cultures and in home swimming pool test kits. It is also used in the (now infrequently performed) phenolsulfonphthalein (PSP) test for estimation of overall blood flow through the kidney.		2.13102,1-benzoxathiole;
arenesulfonate ester;
phenols;
sultone		acid-base indicator;
diagnostic agent;
two-colour indicator
terbutaline
Terbutaline: A selective beta-2 adrenergic agonist used as a bronchodilator and tocolytic.. terbutaline : A member of the class of phenylethanolamines that is catechol substituted at position 5 by a 2-(tert-butylamino)-1-hydroxyethyl group.		2.1310phenylethanolamines;
resorcinols		anti-asthmatic drug;
beta-adrenergic agonist;
bronchodilator agent;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
hypoglycemic agent;
sympathomimetic agent;
tocolytic agent
tulobuterol
[no description available]		2.1310organochlorine compound
diethanolamine
diethanolamine: RN given refers to parent cpd. diethanolamine : A member of the class of ethanolamines that is ethanolamine having a N-hydroxyethyl substituent.		2.0410ethanolamineshuman xenobiotic metabolite
isostearate
16-methylheptadecanoic acid : A methyl-branched fatty acid that is heptadecanoic acid (margaric acid) substituted by a methyl group at position 16.		2.1310branched-chain saturated fatty acid;
long-chain fatty acid;
methyl-branched fatty acid
manganese
Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.		210elemental manganese;
manganese group element atom		Escherichia coli metabolite;
micronutrient
triisopropanolamine
triisopropanolamine: RN given refers to parent cpd		2.4220amino alcohol
diisopropanolnitrosamine
diisopropanolnitrosamine: experimental carcinogen. N,N-bis(2-hydroxypropyl)nitrosamine : A nitrosamine that is dipropylamine in which the hydrogen attached to the nitrogen has been replaced by a nitroso group. It is a genotoxic carcinogen, targeting the lung, liver, thyroid, and kidney.		2.6630diol;
nitrosamine;
secondary alcohol		carcinogenic agent
caprylates
Caprylates: Derivatives of caprylic acid. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain a carboxy terminated eight carbon aliphatic structure.. octanoate : A straight-chain saturated fatty acid anion that is the conjugate base of octanoic acid (caprylic acid); believed to block adipogenesis.		2.1310fatty acid anion 8:0;
straight-chain saturated fatty acid anion		human metabolite;
Saccharomyces cerevisiae metabolite
crotamiton
[no description available]		7.0110
sodium nitrite
Sodium Nitrite: Nitrous acid sodium salt. Used in many industrial processes, in meat curing, coloring, and preserving, and as a reagent in ANALYTICAL CHEMISTRY TECHNIQUES. It is used therapeutically as an antidote in cyanide poisoning. The compound is toxic and mutagenic and will react in vivo with secondary or tertiary amines thereby producing highly carcinogenic nitrosamines.. sodium nitrite : An inorganic sodium salt having nitrite as the counterion. Used as a food preservative and antidote to cyanide poisoning.		2.3820inorganic sodium salt;
nitrite salt		antidote to cyanide poisoning;
antihypertensive agent;
antimicrobial food preservative;
food antioxidant;
poison
ConditionIndicatedRelationship StrengthStudiesTrials
Allergic Contact Dermatitis
[description not available]		02.4220
Dermatitis Medicamentosa
[description not available]		02.3920
Dermatitis, Allergic Contact
A contact dermatitis due to allergic sensitization to various substances. These substances subsequently produce inflammatory reactions in the skin of those who have acquired hypersensitivity to them as a result of prior exposure.		02.4220
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		02.0310
Pregnancy
The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.		02.0310
Experimental Neoplasms
[description not available]		02.3820
Experimental Hepatoma
[description not available]		01.9710
Contact Dermatitis
[description not available]		06.9710
Dermatitis, Contact
A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.		01.9710