methylene bis(4-cyclohexylisocyanate) profile

Methylene bis(4-cyclohexylisocyanate) (also known as MDI or H12MDI) is a diisocyanate used in the production of polyurethane foams, coatings, and elastomers. It is synthesized through the reaction of cyclohexylamine with phosgene. MDI is a highly reactive compound, and its polymerization can produce rigid or flexible foams with different properties. MDI-based polymers are used in a wide range of applications, including insulation, furniture, automotive parts, and construction materials. The high reactivity of MDI can pose a health hazard, as it can cause respiratory irritation and allergic reactions. Therefore, its handling requires appropriate safety precautions.'

methylene bis(4-cyclohexylisocyanate): used in manufacture of polyurethane foam; RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

dicyclohexylmethane-4,4'-diisocyanate : A diisocyanate consisting of dicyclohexylmethane with two isocyanate groups at the 4- and 4'-positions. [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 Source	ID
PubMed CID	21202
CHEMBL ID	1878565
CHEBI ID	53216
SCHEMBL ID	22543
SCHEMBL ID	5902920
SCHEMBL ID	5903114
SCHEMBL ID	8733246
SCHEMBL ID	6318341
SCHEMBL ID	10507329
SCHEMBL ID	19751835
SCHEMBL ID	22958492
SCHEMBL ID	24783191
MeSH ID	M0061489

Synonyms (96)

Synonym
4,4'-methylenedi(cyclohexyl isocyanate)
cyclohexane, 1,1'-methylenebis[4-isocyanato-
isocyanic acid, methylenedi-4,1-cyclohexylene ester
methylene bis-(4-cyclohexylisocyanate)
brn 2217800
hylene w
cp 99173
dicyclohexylmethane-4,4'-diisocyanate
dicyclohexylmethane 4,4'-diisocyanate
cyclohexane, 1,1'-methylenebis(4-isocyanato-
1,1-methylenebis(4-isocyanatocyclohexane) [diisocyanates]
nacconate h 12
methylene bis(4-cyclohexylisocyanate)
einecs 225-863-2
4,4'-methylenedicyclohexyl diisocyanate
methylenebis(4-cyclohexylisocyanate)
4,4'-diisocyanatodicyclohexylmethane
hsdb 7189
bis(4-isocyanatocyclohexyl)methane
5124-30-1
NCGC00164262-01
1,1'-methylenebis(4-isocyanatocyclohexane)
dicyclohexylmethane-4,4'-di-isocyanate
CHEBI:53216 ,
1-isocyanato-4-[(4-isocyanatocyclohexyl)methyl]cyclohexane
D2380
4,4'-methylenebis(cyclohexyl isocyanate)
AKOS000120188
z717id22kx ,
cyclohexane, 1,1'-methylenebis(4-isocyanato-, (trans,trans)-
unii-z717id22kx
4,4'-diisocyanatodicyclohexylmethane, trans,trans-
13622-90-7
28605-81-4
cyclohexane, 1,1'-methylenebis(isocyanato-
NCGC00255393-01
cas-5124-30-1
tox21_301473
dtxsid3027588 ,
dtxcid307588
1,1-methylene bis(4-isocyanatocyclohexane)
ec 225-863-2
4ct385m7k2 ,
unii-4ct385m7k2
1,1-methylenebis(4-isocyanatocyclohexane)
FT-0635549
EPITOPE ID:113239
cyclohexane, 1,1'-methylenebis[4-isocyanato-, (trans,trans)-
isocyanic acid, methylenedi-4,1-cyclohexylene ester, trans,trans-
trans,trans-4,4'-diisocyanatodicyclohexylmethane
trans-trans-methylenebis(4-cyclohexylisocyanate)
4,4'-diisocyanatodicyclohexylmethane, cis,cis-
p815vnf99i ,
4,4'-diisocyanatodicyclohexylmethane, cis,trans-
6y80aja84r ,
cis,cis-4,4'-diisocyanatodicyclohexylmethane
unii-6y80aja84r
isocyanic acid, methylenedi-4,1-cyclohexylene ester, cis,cis-
18937-00-3
cis-cis-methylene bis(4-cyclohexylisocyanate)
cis,trans-4,4'-diisocyanatodicyclohexylmethane
cyclohexane, 1,1'-methylenebis(4-isocyanato-, (cis(cis))-
isocyanic acid, methylenedi-4,1-cyclohexylene ester, cis,trans-
unii-p815vnf99i
cyclohexane, 1,1'-methylenebis(4-isocyanato-, (cis(trans))-
17901-48-3
cis-trans-methylene bis(4-cyclohexylisocyanate)
SCHEMBL22543
SCHEMBL5902920
SCHEMBL5903114
4,4'-methylenebis-(cyclohexyl isocyanate)
KORSJDCBLAPZEQ-UHFFFAOYSA-N
4,4'-diisocyanato dicyclohexylmethane
methylene-bis-(4-cyclohexyl isocyanate)
SCHEMBL8733246
SCHEMBL6318341
CHEMBL1878565
methylene-bis(4-cyclohexylisocyanate)
SCHEMBL10507329
F2191-0303
dicyclohexylmethane-4,4'-diiso cyanate
mfcd00015405
hmdi, analytical standard
(trans,trans)-1,1'-methylenebis[4-isocyanatocyclohexane]
DTXSID30891145
dicyclohexyl-methane-4,4'-diisocyanate
SCHEMBL19751835
Q1562648
Q27295091
Q27286344
Q27265708
BS-42301
SCHEMBL22958492
156515-75-2
F87466
SCHEMBL24783191

Excerpt	Relevance	Reference
" In mice, as well as in guinea pigs, a dose-response relationship was apparent between the sensitizing dose and both severity of response and number of animals responding."	( Use of dose-response data to compare the skin sensitizing abilities of dicyclohexylmethane-4,4'-diisocyanate and picryl chloride in two animal species. Karol, MH; Stadler, JC, 1985)	0.27

Role	Description
allergen	A chemical compound, or part thereof, which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
[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]

Class	Description
diisocyanate	An isocyanate compound containing two isocyanate functional groups. Manufactured for reaction with polyols in the production of polyurethanes.
[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	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
RAR-related orphan receptor gamma	Mus musculus (house mouse)	Potency	0.6113	0.0060	38.0041	19,952.5996	AID1159521
GLI family zinc finger 3	Homo sapiens (human)	Potency	43.2771	0.0007	14.5928	83.7951	AID1259369; AID1259392
AR protein	Homo sapiens (human)	Potency	50.1187	0.0002	21.2231	8,912.5098	AID588515
glucocorticoid receptor [Homo sapiens]	Homo sapiens (human)	Potency	48.9662	0.0002	14.3764	60.0339	AID720691
retinoic acid nuclear receptor alpha variant 1	Homo sapiens (human)	Potency	23.3186	0.0030	41.6115	22,387.1992	AID1159552; AID1159555
pregnane X nuclear receptor	Homo sapiens (human)	Potency	54.4827	0.0054	28.0263	1,258.9301	AID1346982
nuclear factor of kappa light polypeptide gene enhancer in B-cells 1 (p105), isoform CRA_a	Homo sapiens (human)	Potency	48.9662	19.7391	45.9784	64.9432	AID1159509
thyroid hormone receptor beta isoform a	Homo sapiens (human)	Potency	0.0794	0.0100	39.5371	1,122.0200	AID588547
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	8 (29.63)	18.7374
1990's	4 (14.81)	18.2507
2000's	7 (25.93)	29.6817
2010's	8 (29.63)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (3.57%)	6.00%
Case Studies	3 (10.71%)	4.05%
Observational	0 (0.00%)	0.25%
Other	24 (85.71%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	2.06	1	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
nitroglycerin Nitroglycerin: A volatile vasodilator which relieves ANGINA PECTORIS by stimulating GUANYLATE CYCLASE and lowering cytosolic calcium. It is also sometimes used for TOCOLYSIS and explosives.. nitroglycerol : A nitrate ester that is glycerol in which nitro group(s) replace the hydrogen(s) attached to one or more of the hydroxy groups.. nitroglycerin : A nitroglycerol that is glycerol in which the hydrogen atoms of all three hydroxy groups are replaced by nitro groups. It acts as a prodrug, releasing nitric oxide to open blood vessels and so alleviate heart pain.	1.99	1	nitroglycerol	explosive; muscle relaxant; nitric oxide donor; prodrug; tocolytic agent; vasodilator agent; xenobiotic
bisphenol a 4,4'-isopropylidene diphenol: stimulates proliferative responses and cytokine productions of murine spleen cells and thymus cells in vitro. bisphenol : By usage, the methylenediphenols, HOC6H4CH2C6H4OH, commonly p,p-methylenediphenol, and their substitution products (generally derived from condensation of two equivalent amounts of a phenol with an aldehyde or ketone). The term also includes analogues in the the methylene (or substituted methylene) group has been replaced by a heteroatom.. bisphenol A : A bisphenol that is 4,4'-methanediyldiphenol in which the methylene hydrogens are replaced by two methyl groups.	2.1	1	bisphenol	endocrine disruptor; environmental contaminant; xenobiotic; xenoestrogen
picryl chloride Picryl Chloride: A hapten that generates suppressor cells capable of down-regulating the efferent phase of trinitrophenol-specific contact hypersensitivity. (Arthritis Rheum 1991 Feb;34(2):180).. 1-chloro-2,4,6-trinitrobenzene : The C-nitro compound that is chlorobenzene with three nitro substituents in the 2-, 4- and 6-positions.	1.96	1	C-nitro compound; monochlorobenzenes	allergen; epitope; explosive; hapten
tolonium chloride Tolonium Chloride: A phenothiazine that has been used as a hemostatic, a biological stain, and a dye for wool and silk. Tolonium chloride has also been used as a diagnostic aid for oral and gastric neoplasms and in the identification of the parathyroid gland in thyroid surgery.. tolonium chloride : An organic chloride salt having 3-amino-7-(dimethylamino)-2-methylphenothiazin-5-ium (tolonium) as the counterion. It is a blue nuclear counterstain that can be used to demonstrate Nissl substance and is also useful for staining mast cell granules, both in metachromatic and orthochromatic techniques.	2.04	1
4,4'-diphenylmethane diisocyanate 4,4'-diphenylmethane diisocyanate: used as a hardening agent incorporated in polyurethanes. diphenylmethane-4,4'-diisocyanate : A diisocyanate consisting of diphenylmethane with two isocyanate groups at the 4- and 4'-positions.	4.2	5	diisocyanate	allergen; hapten
4,4'-diaminodiphenylmethane 4,4'-diaminodiphenylmethane: RN given refers to parent cpd; structure. 4,4'-diaminodiphenylmethane : An aromatic amine that is diphenylmethane substituted at the 4-position of each benzene ring by an amino group.	2.15	1	aromatic amine	allergen; carcinogenic agent
diphenylmethane diphenylmethane : A diarylmethane that is methane substituted by two phenyl groups.	2.15	1	diarylmethane
epichlorohydrin Epichlorohydrin: A chlorinated epoxy compound used as an industrial solvent. It is a strong skin irritant and carcinogen.. epichlorohydrin : An epoxide that is 1,2-epoxypropene in which one of the methyl hydrogens is substituted by chlorine.	2.1	1	epoxide; organochlorine compound
1,4-butanediol butane-1,4-diol : A butanediol that is butane in which one hydrogen of each of the methyl groups is substituted by a hydroxy group. A colourless, water-miscible, viscous liquid at room temperature (m.p. 16degreeC) with a high boiling point (230degreeC), it is mainly used for the production of other organic chemicals, particularly the solvent oxolane (also known as tetrahydrofuran or THF).	2.15	1	butanediol; glycol	neurotoxin; prodrug; protic solvent
perfluorooctanoic acid perfluorooctanoic acid: RN given refers to parent cpd. perfluorooctanoic acid : A fluoroalkanoic acid that is perfluorinated octanoic acid.	2.1	1	fluoroalkanoic acid	carcinogenic agent; endocrine disruptor; environmental contaminant; surfactant; xenobiotic
toluene 2,4-diisocyanate Toluene 2,4-Diisocyanate: Skin irritant and allergen used in the manufacture of polyurethane foams and other elastomers.. toluene 2,4-diisocyanate : A toluene meta-diisocyanate in which the isocyanato groups are at positions 2 and 4 relative to the methyl group on the benzene ring.	1.97	1	toluene meta-diisocyanate	allergen; hapten
1,6-hexamethylene diisocyanate hexamethylene diisocyanate : A diisocyanate compound with the two isocyanates linked by a hexane-1,6-diyl group.	2.72	3	diisocyanate	allergen; hapten
hydroxyethyl methacrylate hydroxyethyl methacrylate: many of cited refs are for gel which refers to polymeric form of above cpd: POLYHYDROXYETHYL METHACRYLATE. 2-hydroxyethyl methacrylate : An enoate ester that is the monomethacryloyl derivative of ethylene glycol.	1.99	1	enoate ester	allergen; polymerisation monomer
ethyldimethylaminopropyl carbodiimide Ethyldimethylaminopropyl Carbodiimide: Carbodiimide cross-linking reagent.	2.04	1
gamma-glycidoxypropyltrimethoxysilane 3-glycidyloxypropyltrimethoxysilane: used to immobilize carbonic anhydrase into mesoporous supports; structure in first source	2.1	1
isophorone diamine isophorone diamine: curing agent for polymers; structure given in first source; RN given refers to parent cpd	2.01	1
atorvastatin [no description available]	2.17	1	aromatic amide; dihydroxy monocarboxylic acid; monofluorobenzenes; pyrroles; statin (synthetic)	environmental contaminant; xenobiotic
metaperiodate Periodic Acid: A strong oxidizing agent.	2.04	1	iodine oxoacid
n,n'-(1,2-dihydroxyethylene)bisacrylamide [no description available]	2.15	1
cyanates Cyanates: Organic salts of cyanic acid containing the -OCN radical.. cyanates : Salts and esters of cyanic acid, HOC#N; compounds carrying the cyanate functional group -O-C#N.. isocyanates : Organonitrogen compounds that are derivatives of isocyanic acid; compounds containing the isocyanate functional group -N=C=O (as opposed to the cyanate group, -O-C#N).	5.74	27
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.	2.1	1	fatty acid anion 8:0; straight-chain saturated fatty acid anion	human metabolite; Saccharomyces cerevisiae metabolite
metaperiodate metaperiodate: RN given refers to periodic acid, Na salt; structure. periodate : A monovalent inorganic anion obtained by deprotonation of periodic acid.	2.04	1	iodine oxoanion; monovalent inorganic anion
isophorone diisocyanate [no description available]	2.71	3	diisocyanate
elastin [no description available]	2.05	1	oligopeptide
dithioerythritol [no description available]	2.08	1	1,4-dimercaptobutane-2,3-diol	reducing agent
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.1	1	cyclodextrin
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	2.06	1	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger
oxazolone Oxazolone: Immunologic adjuvant and sensitizing agent.	1.98	1
ascorbic acid Ascorbic Acid: A six carbon compound related to glucose. It is found naturally in citrus fruits and many vegetables. Ascorbic acid is an essential nutrient in human diets, and necessary to maintain connective tissue and bone. Its biologically active form, vitamin C, functions as a reducing agent and coenzyme in several metabolic pathways. Vitamin C is considered an antioxidant.. L-ascorbic acid : The L-enantiomer of ascorbic acid and conjugate acid of L-ascorbate.. L-ascorbate : The L-enantiomer of ascorbate and conjugate base of L-ascorbic acid, arising from selective deprotonation of the 3-hydroxy group. Required for a range of essential metabolic reactions in all animals and plants.. vitamin C : Any member of a group of vitamers that belong to the chemical structural class called butenolides that exhibit biological activity against vitamin C deficiency in animals. The vitamers include L-ascorbic acid and its salt, ionized and oxidized forms.	2.15	1	ascorbic acid; vitamin C	coenzyme; cofactor; flour treatment agent; food antioxidant; food colour retention agent; geroprotector; plant metabolite; skin lightening agent

Condition	Relationship Strength	Studies
Allergic Contact Dermatitis [description not available]	2.46	2
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.	2.46	2
Asthma, Occupational Asthma attacks caused, triggered, or exacerbated by OCCUPATIONAL EXPOSURE.	2.1	1
Recrudescence [description not available]	2.02	1
Foreign-Body Reaction Chronic inflammation and granuloma formation around irritating foreign bodies.	2.02	1
Urinary Incontinence, Stress Involuntary discharge of URINE as a result of physical activities that increase abdominal pressure on the URINARY BLADDER without detrusor contraction or overdistended bladder. The subtypes are classified by the degree of leakage, descent and opening of the bladder neck and URETHRA without bladder contraction, and sphincter deficiency.	2.02	1
Urinary Retention Inability to empty the URINARY BLADDER with voiding (URINATION).	2.02	1
Blood Clot [description not available]	2.04	1
Thrombosis Formation and development of a thrombus or blood clot in the blood vessel.	2.04	1
Contact Dermatitis [description not available]	3.35	7
Dermatitis, Occupational A recurrent contact dermatitis caused by substances found in the work place.	2.36	2
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.	3.35	7
Facial Dermatoses Skin diseases involving the FACE.	1.96	1
Hand Dermatosis [description not available]	1.96	1
Hand Dermatoses Skin diseases involving the HANDS.	1.96	1
Delayed Hypersensitivity [description not available]	2.37	2
Disease, Pulmonary [description not available]	2.66	3
Lung Diseases Pathological processes involving any part of the LUNG.	2.66	3
Diseases, Occupational [description not available]	1.96	1
Eczema, Atopic [description not available]	1.95	1
Dermatitis, Atopic A chronic inflammatory genetically determined disease of the skin marked by increased ability to form reagin (IgE), with increased susceptibility to allergic rhinitis and asthma, and hereditary disposition to a lowered threshold for pruritus. It is manifested by lichenification, excoriation, and crusting, mainly on the flexural surfaces of the elbow and knee. In infants it is known as infantile eczema.	1.95	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.37	2
Airway Hyper-Responsiveness [description not available]	1.97	1

methylene bis(4-cyclohexylisocyanate)

Description

Cross-References

Synonyms (96)

Research Excerpts

Dosage Studied

Roles (1)

Drug Classes (1)

Protein Targets (8)

Potency Measurements

Research

Studies (27)

Market Indicators

Research Demand Index: 27.69

Study Types

methylene bis(4-cyclohexylisocyanate)

Description

Cross-References

Synonyms (96)

Research Excerpts

Dosage Studied

Roles (1)

Drug Classes (1)

Protein Targets (8)

Potency Measurements

Research

Studies (27)

Market Indicators

Research Demand Index: 27.69

Study Types

Related Drugs (30)

Related Conditions (23)