2,2-di(4-methacryloxyphenyl)propane profile

2,2-di(4-methacryloxyphenyl)propane, also known as BisGMA, is a widely used monomer in dental resins. Its synthesis involves the reaction of bisphenol A with methacryloyl chloride. BisGMA exhibits excellent mechanical properties, contributing to the durability and strength of dental materials. It is studied extensively due to its biocompatibility and ability to form strong bonds with tooth structure. BisGMA is often used in combination with other monomers to create a variety of dental resins, including composites, sealants, and adhesives. However, concerns regarding its potential toxicity and allergenicity have led to ongoing research into alternative materials.'

2,2-di(4-methacryloxyphenyl)propane: used in polymers & copolymers of dental materials [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

bisphenol A dimethacrylate : A bisphenol that is bisphenol A condensed with two molecules of methacrylic acid. [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]

ID Source	ID
PubMed CID	76739
CHEBI ID	34579
SCHEMBL ID	30971
MeSH ID	M0043059

Synonym
BIDD:ER0451
bisphenol-a-dimethacrylate (bisdma)
982o8255ne ,
2-propenoic acid, 2-methyl-, 1,1'-((1-methylethylidene)di-4,1-phenylene) ester
unii-982o8255ne
2,2-di(4-methacryloxyphenyl)propane
3253-39-2
bisphenol a dimethacrylate
bisphenol a dimethacrylate, >98%
4,4'-isopropylidenediphenyl dimethacrylate
einecs 221-846-9
2-propenoic acid, 2-methyl-, (1-methylethylidene)di-4,1-phenylene ester
4,4'-isopropylidenediphenol dimethacrylate
2,2-propanediyldi-4,1-phenylene bis(2-methylacrylate)
I0389
[4-[2-[4-(2-methylprop-2-enoyloxy)phenyl]propan-2-yl]phenyl] 2-methylprop-2-enoate
CHEBI:34579
AKOS015913431
propane-2,2-diyldibenzene-4,1-diyl bis(2-methylprop-2-enoate)
propane-2,2-diyldi-4,1-phenylene bis(2-methylacrylate)
diphenylolpropane dimethacrylate
SCHEMBL30971
4-(1-[4-(methacryloyloxy)phenyl]-1-methylethyl)phenyl 2-methylacrylate #
QUZSUMLPWDHKCJ-UHFFFAOYSA-N
2,2-bis(4-methacryloxyphenyl)propane
mfcd00008585
4-(2-{4-[(2-methylprop-2-enoyl)oxy]phenyl}propan-2-yl)phenyl 2-methylprop-2-enoate
AS-70135
4,4'-(propane-2,2-diyl)bis(4,1-phenylene) bis(2-methylacrylate)
(propane-2,2-diyl)di(4,1-phenylene) bis(2-methylprop-2-enoate)
DTXSID80863135
propane-2,2-diylbis(4,1-phenylene) bis(2-methylacrylate)
FT-0748525
Q27116160
2,2-bis(4-hydroxyphenyl)propane dimethacrylate
D91137

Excerpt	Reference	Relevance
" The results suggest that Bis-DMA has adverse effects on the fertility and reproductive systems of male and female mice."	( Reproductive toxic effect of bisphenol A dimethacrylate in mice. Al-Hiyasat, AS; Darmani, H, 2004)	0.32

Role	Description
metabolite	Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[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
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.
enoate ester	An alpha,beta-unsaturated carboxylic ester of general formula R(1)R(2)C=CR(3)-C(=O)OR(4) (R(4) =/= H) in which the ester C=O function is conjugated to a C=C double bond at the alpha,beta position.
[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]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	2 (5.13)	18.7374
1990's	5 (12.82)	18.2507
2000's	15 (38.46)	29.6817
2010's	15 (38.46)	24.3611
2020's	2 (5.13)	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	1 (2.50%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	1 (2.50%)	4.05%
Observational	0 (0.00%)	0.25%
Other	38 (95.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
hydrochloric acid Hydrochloric Acid: A strong corrosive acid that is commonly used as a laboratory reagent. It is formed by dissolving hydrogen chloride in water. GASTRIC ACID is the hydrochloric acid component of GASTRIC JUICE.. hydrogen chloride : A mononuclear parent hydride consisting of covalently bonded hydrogen and chlorine atoms.	2	1	0	chlorine molecular entity; gas molecular entity; hydrogen halide; mononuclear parent hydride	mouse metabolite
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.	2.17	1	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
phosphoric acid phosphoric acid: concise etchant is 37% H3PO4. phosphoric acid : A phosphorus oxoacid that consists of one oxo and three hydroxy groups joined covalently to a central phosphorus atom.	2	1	0	phosphoric acids	algal metabolite; fertilizer; human metabolite; NMR chemical shift reference compound; solvent
4-nonylphenol 4-nonylphenol: structure in first source; see also record for nonylphenol. 4-nonylphenol : A member of the class of phenols that is phenol which is para-substituted with a nonyl group.	2.03	1	0	phenols	environmental contaminant
2,2-bis(4-glycidyloxyphenyl)propane 2,2-bis(4-glycidyloxyphenyl)propane: structure	5.01	3	1	diarylmethane
camphor, (+-)-isomer [no description available]	2.17	1	0	bornane monoterpenoid; cyclic monoterpene ketone	plant metabolite
haloperidol Haloperidol: A phenyl-piperidinyl-butyrophenone that is used primarily to treat SCHIZOPHRENIA and other PSYCHOSES. It is also used in schizoaffective disorder, DELUSIONAL DISORDERS, ballism, and TOURETTE SYNDROME (a drug of choice) and occasionally as adjunctive therapy in INTELLECTUAL DISABILITY and the chorea of HUNTINGTON DISEASE. It is a potent antiemetic and is used in the treatment of intractable HICCUPS. (From AMA Drug Evaluations Annual, 1994, p279). haloperidol : A compound composed of a central piperidine structure with hydroxy and p-chlorophenyl substituents at position 4 and an N-linked p-fluorobutyrophenone moiety.	2.66	3	0	aromatic ketone; hydroxypiperidine; monochlorobenzenes; organofluorine compound; tertiary alcohol	antidyskinesia agent; antiemetic; dopaminergic antagonist; first generation antipsychotic; serotonergic antagonist
4-aminobenzoic acid para-Aminobenzoates: Benzoic acids, salts, or esters that contain an amino group attached to carbon number 4 of the benzene ring structure.. 4-aminobenzoate : An aromatic amino-acid anion that is the conjugate base of 4-aminobenzoic acid.	2.17	1	0	aminobenzoate; aromatic amino-acid anion	Escherichia coli metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
lactose Lactose: A disaccharide of GLUCOSE and GALACTOSE in human and cow milk. It is used in pharmacy for tablets, in medicine as a nutrient, and in industry.. lactose : A glycosylglucose disaccharide, found most notably in milk, that consists of D-galactose and D-glucose fragments bonded through a beta-1->4 glycosidic linkage. The glucose fragment can be in either the alpha- or beta-pyranose form, whereas the galactose fragment can only have the beta-pyranose form.. beta-lactose : The beta-anomer of lactose.	2.08	1	0	lactose
propane Propane: A three carbon alkane with the formula H3CCH2CH3.	2	1	0	alkane; gas molecular entity	food propellant
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.	2.52	2	0	aliphatic nitrile; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent
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.	6.39	15	1	bisphenol	endocrine disruptor; environmental contaminant; xenobiotic; xenoestrogen
methylmethacrylate Methylmethacrylate: The methyl ester of methacrylic acid. It polymerizes easily to form POLYMETHYL METHACRYLATE. It is used as a bone cement.. methyl methacrylate : An enoate ester having methacrylic acid as the carboxylic acid component and methanol as the alcohol component.	1.98	1	0	enoate ester; methyl ester	allergen; polymerisation monomer
pyromellitic acid pyromellitic acid: RN given refers to parent cpd; structure. pyromellitic acid : A tetracarboxylic acid that is benzene substituted by four carboxy groups at positions 1, 2, 4 and 5 respectively.	2.17	1	0	benzoic acids; tetracarboxylic acid
propylparaben Parabens: Methyl, propyl, butyl, and ethyl esters of p-hydroxybenzoic acid. They have been approved by the FDA as antimicrobial agents for foods and pharmaceuticals. (From Hawley's Condensed Chemical Dictionary, 11th ed, p872)	2.06	1	0	benzoate ester; paraben; phenols	antifungal agent; antimicrobial agent
ethylene dimethacrylate ethylene glycol dimethacrylate : The enoate ester that is the 1,2-bis(methacryloyl) derivative of ethylene glycol.	2.47	2	0	enoate ester	allergen; cross-linking reagent; polymerisation monomer
triethylene glycol dimethacrylate [no description available]	6.06	10	1
diethylhexyl phthalate Diethylhexyl Phthalate: An ester of phthalic acid. It appears as a light-colored, odorless liquid and is used as a plasticizer for many resins and elastomers.. bis(2-ethylhexyl) phthalate : A phthalate ester that is the bis(2-ethylhexyl) ester of benzene-1,2-dicarboxylic acid.	2	1	0	diester; phthalate ester	androstane receptor agonist; apoptosis inhibitor; plasticiser
gentian violet Gentian Violet: A dye that is a mixture of violet rosanilinis with antibacterial, antifungal, and anthelmintic properties.. crystal violet : An organic chloride salt that is the monochloride salt of crystal violet cation. It has been used in creams for the topical treatment of bacterial and fungal infections, being effective against some Gram-positive bacteria (notably Staphylococcus species) and some pathogenic fungi (including Candida species) but use declined following reports of animal carcinogenicity. It has also been used for dying wood, silk, and paper, as well as a histological stain.	2	1	0	organic chloride salt	anthelminthic drug; antibacterial agent; antifungal agent; antiseptic drug; histological dye
c.i. 42510 Rosaniline Dyes: Compounds that contain the triphenylmethane aniline structure found in rosaniline. Many of them have a characteristic magenta color and are used as COLORING AGENTS.. basic fuchsin : A four-component mixture of chemically related dyes comprising pararosanilin, rosanilin, magenta II and new fuchsin in varying amounts. rosanilin : A hydrochloride that is the monohydrochloride of 4-[(4-aminophenyl)(4-iminocyclohexa-2,5-dien-1-ylidene)methyl]-2-methylaniline. One of the major constituents of Basic fuchsin, together with pararosanilin, magenta II and new fuchsin.	2	1	0
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.	2.78	3	0	enoate ester	allergen; polymerisation monomer
sodium hydroxide Sodium Hydroxide: A highly caustic substance that is used to neutralize acids and make sodium salts. (From Merck Index, 11th ed)	2	1	0	alkali metal hydroxide
zinc oxide Zinc Oxide: A mild astringent and topical protectant with some antiseptic action. It is also used in bandages, pastes, ointments, dental cements, and as a sunblock.	2.17	1	0	zinc molecular entity
bisphenol a-glycidyl methacrylate Bisphenol A-Glycidyl Methacrylate: The reaction product of bisphenol A and glycidyl methacrylate that undergoes polymerization when exposed to ultraviolet light or mixed with a catalyst. It is used as a bond implant material and as the resin component of dental sealants and composite restorative materials.	4.1	15	0	diarylmethane
4-octylphenol 4-octylphenol: xenoestrogen. 4-octylphenol : A member of the class of phenols that is phenol which is substituted at the para- position by an octyl group.	2.03	1	0	phenols	metabolite; surfactant; xenoestrogen
silver Silver: An element with the atomic symbol Ag, atomic number 47, and atomic weight 107.87. It is a soft metal that is used medically in surgical instruments, dental prostheses, and alloys. Long-continued use of silver salts can lead to a form of poisoning known as ARGYRIA.	2.08	1	0	copper group element atom; elemental silver	Escherichia coli metabolite
zirconium Zirconium: A rather rare metallic element with atomic number 40, atomic weight 91.224, and symbol Zr.	2.08	1	0	titanium group element atom
tricalcium phosphate tricalcium phosphate: a form of tricalcium phosphate used as bioceramic bone replacement material; see also records for alpha-tricalcium phosphate, beta-tricalcium phosphate, calcium phosphate; apatitic tricalcium phosphate Ca9(HPO4)(PO4)5(OH) is the calcium orthophosphate leading to beta tricalcium phosphate Ca3(PO4)2 (b-TCP). calcium phosphate : A calcium salt composed of calcium and phosphate/diphosphate ions; present in milk and used for the mineralisation of calcified tissues.	2.17	1	0	calcium phosphate
camphoroquinone camphoroquinone: a natural monoterpene, non-aromatic quinone; structure given in first source. bornane-2,3-dione : A bornane monoterpenoid that is bicyclo[2.2.1]heptane substituted by methyl groups at positions 1, 7 and 7 and oxo groups at positions 2 and 3.	2.17	1	0	bornane monoterpenoid; carbobicyclic compound
lissamine rhodamine b lissamine rhodamine B: RN given refers to parent cpd; Lissamine Rhodamine B refers to Na salt	2.45	2	0
divinyl benzene [no description available]	2.05	1	0	styrenes
4-nitrophenyl butyrate p-nitrophenyl butyrate : A butyrate ester resulting from the formal condensation of the hydroxy group of 4-nitrophenol with the carboxy group of butyric acid.	2	1	0	butyrate ester; C-nitro compound
2,2-bis-(4-(2-methacryloxyethoxy)phenyl)propane 2,2-bis-(4-(2-methacryloxyethoxy)phenyl)propane: structure given in first source	2.38	2	0
bisphenol a epoxy resin diacrylate ester bisphenol A epoxy resin diacrylate ester: prepolymer in ultraviolet curing inks; structure given in first source	2.36	2	0
pentaerythritol diacrylate monostearate pentaerythritol diacrylate monostearate: structure in first source	2.06	1	0
sulfur Sulfur: An element that is a member of the chalcogen family. It has an atomic symbol S, atomic number 16, and atomic weight [32.059; 32.076]. It is found in the amino acids cysteine and methionine.	2.25	1	0	chalcogen; nonmetal atom	macronutrient
aluminum oxide Aluminum Oxide: An oxide of aluminum, occurring in nature as various minerals such as bauxite, corundum, etc. It is used as an adsorbent, desiccating agent, and catalyst, and in the manufacture of dental cements and refractories.	2.08	1	0
chitosan [no description available]	2.08	1	0
stearates Stearates: Salts and esters of the 18-carbon saturated, monocarboxylic acid--stearic acid.	2.06	1	0

Condition	Relationship Strength	Studies
Caries, Dental [description not available]	2.58	2
Dental Plaque A film that attaches to teeth, often causing DENTAL CARIES and GINGIVITIS. It is composed of MUCINS, secreted from salivary glands, and microorganisms.	2.17	1
Dental Caries Localized destruction of the tooth surface initiated by decalcification of the enamel followed by enzymatic lysis of organic structures and leading to cavity formation. If left unchecked, the cavity may penetrate the enamel and dentin and reach the pulp.	2.58	2
Smear Layer Adherent debris produced when cutting the enamel or dentin in cavity preparation. It is about 1 micron thick and its composition reflects the underlying dentin, although different quantities and qualities of smear layer can be produced by the various instrumentation techniques. Its function is presumed to be protective, as it lowers dentin permeability. However, it masks the underlying dentin and interferes with attempts to bond dental material to the dentin.	2.43	2
Cancer of Mouth [description not available]	2.08	1
Mouth Neoplasms Tumors or cancer of the MOUTH.	2.08	1
Blastocyst Disintegration [description not available]	2.02	1
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	2.02	1
Contact Dermatitis [description not available]	2.36	2
Dermatitis, Occupational A recurrent contact dermatitis caused by substances found in the work place.	1.96	1
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.	2.36	2
Dermatitis, Periocular [description not available]	1.99	1
Mucositis, Oral [description not available]	1.99	1
Stomatitis INFLAMMATION of the soft tissues of the MOUTH, such as MUCOSA; PALATE; GINGIVA; and LIP.	1.99	1
Dermatitis, Perioral A papular eruption of unknown etiology that progresses to residual papular erythema and scaling usually confined to the area of the mouth, and almost exclusively occurring in young women. It may also be localized or extend to involve the eyelids and adjacent glabella area of the forehead (periocular dermatitis). (Dorland, 28th ed)	1.99	1
Breast Cancer [description not available]	2.4	2
Breast Neoplasms Tumors or cancer of the human BREAST.	2.4	2

2,2-di(4-methacryloxyphenyl)propane

Description

Cross-References

Synonyms (36)

Research Excerpts

Toxicity

Roles (1)

Drug Classes (2)

Research

Studies (39)

Market Indicators

Research Demand Index: 11.32

Study Types