Table 1. Identification of 24 phthalates reviewed for this compendium Backbone C Length Chemical Name Common Name CAS no. Molecular Formula MW Structure C1 1,2-Benzenedicarboxylic acid, dimethyl ester Dimethyl phthalate (DMP) * 131-11-3 C10H10O4 194.19 R = CH3 O O R O O R C2 1,2-Benzenedicarboxylic acid, diethyl ester Diethyl phthalate (DEP) * 84-66-2 C12H14O4 222.30 R = C3 (double bond) 1,2-Benzenedicarboxylic acid, di-2-propenyl ester Diallyl phthalate (DAP) 131-17-9 C14H14O4 246.27 R = C3 1,2-Benzenedicarboxylic acid, bis(2-methoxyethyl) ester Bis(2- methoxyethyl) phthalate (DMEP) * 117-82-8 C14H18O6 282.30 R = O C3 1,2-Benzenedicarboxylic acid, bis(2-methylpropyl) ester Diisobutyl phthalate (DIBP) 84-69-5 C16H22O4 278.35 R = C4 1,2-Benzenedicarboxylic acid, dibutyl ester Dibutyl phthalate (DBP) * 84-74-2 C16H22O4 278.34 R = C4, C5 1,2-Benzenedicarboxylic acid, butyl phenylmethyl ester Butylbenzyl phthalate (BBP) * 85-68-7 C19H20O4 312.35 R = R1 =
C8 DnOP -25 390 978 1.92 x 10-5 3 x 10-3 5.22 C7-9 Di-C7-9 PE -48 – -45 398 – 454 965 (6.81 – 93.30) x 10-9 (6.10 – 170) x 10-7 6.9 – 8.6 C8, C9 DINP -50 >400 975 6 x 10-8 6 x 10-5 8.8 (20°C) (20°C) (20°C) C9 DNP No data 413 972 1.33 x 10-2 Insoluble >2.12 (20ºC) (205ºC) C6-10 Di-C6-10 PE -50 250 974 – 979 <1 x 10-4 <2 x 10-4 >3.5 (0.5 kPa) (20°C) (20°C) (20°C) (20°C) C9-11 Di-C9-11 PE -48 – -9 454 – 501 960 (4.97 – 68.10) x 10-10 (<1.70 – 6.10) x 10-7 8.6 – 10.3 C9, C10 DIDP -45 >400 970 5.1 x 10-8 2 x 10-7 8.8 (20°C) (20°C) C10 DIUP -9 501 964 4.97 x 10-10 4.41 x 10-9 10.3 C11 DUP -9 501 954 4.97 x 10-10 4.41 x 10-9 10.3 C12-rich DITDP -37 501 950 3.63 x 10-11 7 x 10-11 12.1 C13 DTDP -37 501 950 3.63 x 10-11 7 x 10-11 12.1
C8 DnOP Rat: 53700 Guinea pig: 75 (mL/kg bw) ME ME insufficient data negative C7-9 Di-C7-9 PE Rat: >15000 – >20000 negative negative negative C8, C9 DINP Rat: >10000 (CAS 68515-48- 0); >40000 (CAS 28553-12- 0) Rabbit: >3160 (CAS 68515-48- 0) Rat, 4h: >4.4 ME ME negative C9 DNP Rat: >2000 Insufficient data Insufficient data C6-10 Di-C6-10 PE Rat: >2000 ME ME C9-11 Di-C9-11 PE Rat: >6200 – 19700 negative negative negative C9, C10 DIDP Rat: >29100 Rat: >2910 Rat, 4h: >12.54 ME ME negative C10 DIUP Rat: >15800 negative C11 DUP Rat: >15800 Rat, 6h: >1.8 negative ME negative C12-rich DITDP Rat: >10000 Rabbit: > 3160 ME ME negative C13 DTDP Rat: >2000 ME – minimal effects Blank cells – no data LLNA – local lymph node assay
C4, C5 BBP Rat: 400: atrophy of testis, seminal vesicle and epididymis Two generation study Rat: 100: ↓ body weight and AGD C4 (ring) DCHP Rat: 80-107 (m-f): ↓ sperm head counts and focal seminiferous tubule atrophy in F1 males Rat: 80-107 (m-f): ↓ AGD & retained nipples in F2 males C5-6 DIHP No data No data C6 DnHP 380: ↓ number of litters/pair, live pups/litter and proportion of pups born alive 380: ↑ pup mortality C6-rich DiHepP 419-1360 (m-f): ↓ reproductive organ weight Developmental study: 750: ↑ resorptions and malformations Two generation study: 222-750 (m-f): ↓ AGD in F2 C6 DEHP 140: ↓ fertility 14: ↓ testes wt, seminiferous tubule atrophy C7 DIOP No data No data C8 DnOP NE NE C7-9 Di-C7-9 PE NE 1000: ↑ skeletal variations (lumbar ribs) C8, C9 DINP Rat: 966: ↓ live birth and survival indices Mouse: 742 (m): ↓ testes weight Two generation study: Rat: 159-395 (m-f): ↓ pup weight at weaning Developmental study: Rat: 750: ↑ areolas/nipples in males; ↑ male reproductive malformations 1000: ↑ skeletal and visceral variations
C9 DNP No data No data C6-10 Di-C6-10 PE Rat: 450 (F0): ↓ seminal vesicle weight Rat: 450: ↓ litter survival, ↓ pup weight C9-11 Di-C9-11 PE NE Rat: 500: ↑ skeletal variations (lumbar ribs) C9, C10 DIDP NE Two generation study: Rat: 134-352 (0.2%): ↓ pup survival in F2 Developmental study: Rat: 1000: ↑ skeletal variations (cervical and lumbar ribs) C10 DIUP No data No data C11 DUP No data No data C12-rich DITDP No data No data C13 DTDP NE NE 1 LOAEL derived from exposure to adult male. F1 i.e. including prenatal exposure included for comparison. f – female; m – male; NE – not established
C6 DEHP Rat: 30600 – >40000 Rabbit: 24750 Rat: >10.62 ME ME Insufficient data negative Non-genotoxic Rat: LOAEL = 146.6; NOAEL = 28.9; Liver, kidney. LOAEL = 37.6; NOAEL= 3.7; Testes. F344 rat: LOAEL = 146.6; NOAEL = 28.9; Adenomas, carcinomas, MCL. Sprague-Dawley rat: Adenomas, carcinomas; benign Leydig cell tumours. Mouse: LOAEL = 292; NOAEL = 98; Adenomas and carcinomas. Syrian golden hamster: Inhalation: negative. 140: ↓ Fertility. 14: ↓ testes wt, seminiferous tubule atrophy. C7 DIOP Rat: >22000 Rabbit: >3160 ME negative Unlikely to be genotoxic Insufficient data Negative in vitro. C8 DnOP Rat: 53700 bw Guinea pig: 75 ME ME Insufficient data negative Non-genotoxic Rat: LOAEL = 350; NOAEL = 37; Liver, thyroid Rat: Insufficient data. NE NE C7-9 Di-C7-9 PE Rat: >15000 – >20000 negative negative negative Unlikely to be genotoxic Rat: LOAEL = 120 NOAEL = 60 Liver, testes, blood, kidney NE > 1000 1000: ↑ Skeletal variations (lumbar ribs). C8, C9 DINP Rat: Rabbit: Rat, 4h: ME ME negative Non-genotoxic Rat: Rat: Mouse: Rat: >10000 >3160 >4.4 LOAEL = 358-442 (m- LOAEL = 358-442 742 (m): 159-395 (m-f): (CAS (CAS f); (m-f); ↓ Testes weight. ↓ Pup weight at 68515- 68515- NOAEL = 88-108 (m- NOAEL = 88-108 (m- weaning. 48-0); 48-0) f); f); Rat: >40000 Liver, kidney. ↑ MCL 966: (CAS ↓ live birth and 28553- Mouse: survival indices 12-0) LOAEL = 335 (f) &
742 (m); NOAEL = 112 (f) & 275 (m); ↑ Hepatocellular adenomas and carcinomas combined. Positive in vitro (1 of 7 studies). C9 DNP Rat: > 2000 Insufficient data Insufficient data Unlikely to be genotoxic Insufficient data. C6-10 Di-C6-10 PE Rat: >2000 ME ME Unlikely to be genotoxic Rat: LOAEL = 45; No NOAEL assigned; Liver, kidney. Negative in vitro. Rat: 450 (F0): ↓ Seminal vesicle weight Rat: 450: ↓ Litter survival, ↓ pup weight C9-11 Di-C9-11 PE Rat: >6200 – 19700 negative negative negative Unlikely to be genotoxic Rat: LOAEL = 1000; NOAEL = 500; Liver NE Rat: 500: ↑ Skeletal variations (lumbar ribs). C9, C10 DIDP Rat: >29100 Rat: >2910 Rat, 4h: >12.54 ME ME negative Non-genotoxic Rat: LOAEL = 120; NOAEL = 60; Liver, kidney Dog: LOAEL=75 mg/kg bw/d: ↑ liver weight (low reliability study) Positive in vitro (1 of 2 studies). NE 134-352: ↓ Pup survival in F2 C10 DIUP Rat: >15800 negative Unlikely to be genotoxic Negative in vitro. C11 DUP Rat: >15800 Rat, 6h: >1.8 negative ME negative Non-genotoxic Rat: LOAEL = 1145; NOAEL = 282; Liver, kidney C12-rich DITDP Rat: >10000 Rabbit: >3160 ME ME negative Unlikely to be genotoxic C13 DTDP Rat: Non-genotoxic Rat: NE NE