Review Article

Endocrine-Disrupting Chemicals: Associated Disorders and Mechanisms of Action

Table 1

Some xenoestrogens, xenoandrogens, antiestrogens, and antiandrogens.

SubstanceSome data on occurrence, useaReferences mentioning xenooestrogenic activity References mentioning xenoandrogenic activityReferences mentioning antiestrogenic activityReferences mentioning antiandrogenic activity

Naturally occurring substances

20S-ProtopanaxadiolGastrointestinal metabolic product of ginsenosides[20]
Alpha-zearalenolMetabolite of zearalenone, used as growth promoter in beef cattle in certain non-European Union countries[21]
ApigeninFlavonoid phytoestrogen[22]
FerutinineSesquiterpenoid, in plants of Umbelliferae family[23]
FormononetinIsoflavonoid, in red clover and soy extracts[24]
GenisteinIsoflavonoid, in red clover and soy extracts[24][25]
KaempferolFlavonoid phytoestrogen[22]
Methoxylated brominated diphenyl ethersOccur naturally in marine organisms[26][26]
ZearalenoneMycotoxin, food contaminant[21]

Industrial products and pollutants including organohalogens, plastic components, detergents

3,9-Dihydroxy-benz[a]anthracenePotential metabolite of benz[a]anthracene
(PAH, mainly < incomplete combustion)
[27]
3-MethylcholanthrenePAH, mainly < incomplete combustion[28][29]
4-n-OctylphenolIntermediate in production of and degradation product of octylphenol ethoxylates used to in rubber, in pesticides and paints[22, 30, 31]
4-NonylphenolPrecursor to and degradation product of commercially important detergents[30]
4-n-PropylphenolDegradation product of surfactants[31]
4-Tert-butyl 2-methylphenolIndustrial product and environmental contaminant[22]
4-Tert-octylphenolUsed in the manufacture of nonionic surfactants[22, 31, 32]
7,12-Dimethyl-benz(a)anthracenePAH, mainly < incomplete combustion [33]
BenzotriazoleAnticorrosive agent used in aircraft de-icing, antifreeze fluids, and dishwasher detergents[34]
Benzyl butyl phthalatePlasticizer for polyvinyl chloride in vinyl floor tiles, vinyl foam, and carpet backing, in cellulosic resins[35]
Bisphenol AUsed in the production of polycarbonate plastic and epoxy resins used as coatings on the inside of food and beverage cans[22, 36, 37]
DibutylphthalateMainly used as plasticiser, also in paints, inks, and cosmetics[35]
DichlorostyreneIntermediate in chemical industry[38]
DodecylphenolUsed in phenol resins in adhesives and paints[31, 39]
NonylphenolsPrecursor to and degradation product of commercially important detergents[22, 31, 32][40]
Polybrominated biphenyl ethers (PBDEs)Flame retardants used in plastics, foams, building materials, electronics, furnishings, motor vehicles[26, 41, 42][43, 44]
Polychlorinated biphenyls (PCBs) (some congeners)Industrial products, used as dielectric and coolant fluids[4550][51][52, 53][54]

Substances used in personal care products

3-Benzylidene camphor UV filters, used in sunscreens and cosmetics[55][55][55]
4,4-Dihydroxy-benzophenoneUV filter, used in sunscreens and cosmetics[55][55]

4-Hydroxybenzoic acid n-butyl ester,
4-hydroxybenzoic acid ethyl ester,
4-hydroxybenzoic acid propyl ester
Preservatives in foods, drugs, and personal products[56]

4-HydroxybenzophenoneMetabolite of UV filter, used in sunscreens and cosmetics[55][55]
4-Methylbenzylidene camphorUV filters, used in sunscreens and cosmetics[55][55]
Benzophenone-1UV filter, used in sunscreens and cosmetics[55][55]
Benzophenone-2UV filter, used in sunscreens and cosmetics[55, 57][55][55]
Benzophenone-3UV filter, used in sunscreens and cosmetics[55][55][55]
Benzophenone-4UV filter, used in sunscreens and cosmetics[55][55, 58][55]
Benzyl salicylateUV filter, used in sunscreens and cosmetics[55][55][55]
Ethoxylated ethyl 4-amino benzoateUV filter, used in sunscreens and cosmetics[55]
Ethyl-4-aminobenzoateUV filter, used in sunscreens and cosmetics[55][55]

Eusolex 2292,
Eusolex 6300,
Eusolex 6007,
Eusolex HMS
UV filter, used in sunscreens and cosmetics[56, 59]

Galaxolide (HHCB)Fragrance, used in sunscreens and cosmetics[56][60][60]
HomosalateUV filter, used in sunscreens and cosmetics[55][55][55]
Isopentyl-4-methoxycinnamateUV filter, used in sunscreens and cosmetics[55][55][55]
OctocryleneUV filter, used in sunscreens and cosmetics[55][55][55]
Octyl dimethyl para amino benzoateUV filter, used in sunscreens and cosmetics[55][55]
Octyl salicylateUV filter, used in sunscreens and cosmetics[55][55][55]
Octyl-methoxycinnamateUV filters, used in sunscreens and cosmetics[55][55][55]
Para amino-benzoic acidUV filter, used in sunscreens and cosmetics[55]
Phenyl salicylateUV filters, used in sunscreens and cosmetics[55][55][60]
Tonalide (AHTN)[60][60]

Pesticides

2,4,5-Trichloro-phenoxyacetic acidHerbicide, defoliant used in Agent Orange in Vietnam[61]
3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropene carboxylic acidPyrethroid insecticide metabolite[62]
3-Phenoxybenzoic acidPyrethroid insecticide metabolite[62]
AlachlorAcid amide herbicide against grasses and broadleaf weeds. Use as herbicide banned in European Union (2006)[63]
Aldrin,Organochlorine insecticide, widely used until 1970s[63][61][64]
AtrazineStill widely used triazine herbicide, banned in the European Union[65]
Azinphos-methylOrganophosphate insecticide, banned in the European Union (2006)[66]
BenomylCarbamate fungicide has been used on fruits[61]
BromopropylateCarbinol acaricide, used on fruits and legumes, in viticulture[63][63, 66]
CarbarylCarbamate insecticide, widely used in gardens, agriculture, and forestry[61]
ChlomethoxyfenDiphenyl ether herbicide, used on rice[63]
Chlordane,Organochlorine pesticide, banned in USA in 1988[61, 63][63, 64]
ChlordeconeOrganochlorine insecticide and fungicide, banned by the Stockholm Convention on persistent organic pollutants[22, 61][61]
ChlornitrofenDiphenyl ether herbicide[63]
ChlorprophamCarbamate herbicide and plant growth regulator[66]
ChlorpyriphosOrganophosphorus insecticide, highly used on corn and fruit trees, still frequently used in Danish greenhouses in 2001[63, 67, 68]
CycloprothrinPyrethroid insecticide used in agriculture[62]
CyfluthrinPyrethroid insecticide, agriculture, home, garden[63][62][63]
Cyhalothrinpyrethroid insecticide, agriculture, home, garden[63][66]
Cypermethrin, Pyrethroid insecticide, in agriculture, home, garden [63, 69]
CyprodinilFungicide used in agriculture and on fruit[66]
DDEDDT metabolite[63, 66]
DDT,Organochlorine pesticide. Banned[22, 61, 63][63, 64]
DeltamethrinPyrethroid insecticide, widely used, still frequently used in Danish greenhouses in 2001[67][63]
DichlorvosOrganophosphate insecticide widely used to control household pests, also on outdoor fruit, and vegetable crops. Frequently used in Danish greenhouses in 2001[67]
DicofolOrganochlorine pesticide for mite control on agricultural crops, ornamentals, and around buildings[63][63, 66]
DieldrinOrganochlorine pesticide, now banned in many countries[61, 63, 67][63, 64, 67]
DimethomorphCinnamic acid fungicide, used in agriculture (potatoes)[66]
Endosulfan, Organochlorine insecticide, banned by the Stockholm Convention (2011)[61, 63, 67, 68, 70][61][63, 64, 66, 67, 69]
Endrin Organochlorine pesticide, used in agriculture. Now banned in many countries[61, 63][61][64]
EthoxyquinQuinoline-based antioxidant used as a food preservative (E324) and a pesticide[66]
EtofenproxPyrethroid insecticide used in homes (pet and foggers)[62]
FenarimolHeterocyclic organochlorine fungicide, used on ornamentals, trees, horticulture (frequently used in Danish greenhouses in 2001)[63, 67, 70][63, 67, 70]
FenbuconazoleTriazole fungicide used in agriculture, fruit [61]
FenhexamidFungicide, used on fruit, ornamentals, trees[66]
FenitrothionOrganophosphorus insecticide, agriculture, grain storage[66]
FenthionOrganothiophosphate insecticide, avicide, and acaricide, widely used in sugar cane, rice, field corn, beets, pome and stone fruit, citrus fruits, pistachio, cotton, olives, coffee, cocoa, vegetables, and vines[71]
FenvaleratePyrethroid pesticide, agriculture, home, garden[61, 63][63]
FludioxonilFungicide used on sowing-seed, vegetables, fruits, and ornamentals[66]
ImazalilImidazole fungicide: sowing seed, potatoes, and fruits after harvesting[66]
LindaneOrganochlorine insecticide, used to treat lice and scabies[64]
LinuronPhenylureum herbicide: horticulture[66]
MethiocarbCarbamate insecticide, still frequently used in Danish greenhouses in 2001[63, 67, 68][63, 66, 67]
MethoxychlorOrganochlorine pesticide, used on crops, ornamentals, livestock, and pets against insects. Banned in the USA (2003) and European Union (2002)[22, 61, 63, 67][61, 63][63, 64]
MetolachlorChloroacetanilide herbicide, grass and broadleaf weed control in agriculture[63]
O-PhenylphenolFungicide, generally applied after harvest; used for waxing citrus fruits. As a food additive, it has E number E231[66]
PentachlorophenolOrganochlorine pesticide: herbicide, insecticide, fungicide, antifouling paint, preservation of wood. Use now restricted[61][64]
PermethrinPyrethroid insecticide, agriculture, home, garden[63][62][69]
PirimicarbCarbamate insecticide: vegetable, cereal, and orchard crops[68]
Pirimiphos-methylPhosphorothioate insecticide: postharvest insecticide used on stored corn and sorghum grain and seed[66]
ProchlorazImidazole-type foliar fungicide: gardening and agriculture, still frequently used in Danish greenhouses in 2001.[72, 73][60, 66, 67]
ProcymidoneDicarboximide fungicide: preharvest spray or postharvest dip of lupins, grapes, stone fruit, strawberries[66]
PropamocarbCarbamate fungicide: horticulture, ornamentals, agriculture[68]
PyrazoxyfenBenzoylpyrazole herbicide[63]
PyrimethanilFungicide: fruit,vineyards[66]
QuinoxyfenFungicide: cereals, beets, strawberries, some berries[66]
TebuconazoleTriazole fungicide: agriculture. Assessed by the Swedish Chemicals Agency as potentially toxic;[66]
TetramethrinPyrethroid insecticide: Primarily pressurized aerosols in household, industrial, commercial, and institutional settings[74]
Tolclofos-methylOrganophosphorous fungicide, still frequently used in Danish greenhouses in 2001[63, 67, 68]
ToxapheneOrganochlorine insecticide (banned in many countries)[61, 68]
Trans-nonachlorOrganochlorine insecticide: agriculture[61][64]
tribenuron-methylHerbicide: grains; still frequently used in Danish greenhouses in 2001[67]
Triflumizole Conazole fungicide: plant protection[63]
VinclozolinDicarboximide fungicide, used on fruits and vegetables, still frequently used in Danish greenhouses in 2001. Use now strictly regulated[61][63, 66, 67]

aThese data are intended to give some indication, but are far from complete.