Group D-7

化学構造　(Chemical Structure)

● Diethylene triamine （ジエチレントリアミン）
　　　CAS： 111-40-0　Industry/Solvent　MW: 103.17

AM

Sal./E.coli

Min ( 0.625 mg/plate, -S9); spa= 81.6 (E. coli)

○w

1)

1) Ministry of Labour, Jpan: Mutagenicity Test Data of Exist. Chem. Subst., Suppl. 2 (2000) (Tables in English)
　
USA-NTP Genotoxicity Screening：
○　AmesTest ：　□

● Diethylfumarate（フマル酸ジエチル）　
　　　623-91-6　　Industry 　 172.20

AM	Sal./ E. coli	Max( 5.0 mg/plate, ±S9)	□	1)
CA	CHL/IU	Min ( 0.013　mg/ml, -Ｓ9), 24h; Poly also	○	1)

1) Ministry of Health & Welfare, Japan: Tox. Test. Rep. of Environ. Chem., Vol. 2, 125 (1995) (Tables in English)

● Di (2-ethylhexyl) phthalate （ジ(2-エチルヘキシル)フタレート）(Dietyl phthalate; DEHP; DOP)
　　　 117-81-7　　 Industry　　 390.56

AM	Sal./ E, coli	Max ( 5.0 mg/plate, ±S9)	□	1)
AM	Sal.	Max ( 5.0 mg/plate, ±S9)	□	2-4)
AM	E, coli	Max ( 5.0 mg/plate, ±S9)	□	3)
CA	CHL/IU	Max (0.25　mg/ml, -Ｓ9), 24-48h	□	5)
CA	Rat hepatocytes	Max (?)	□	6)
CA	CHO	Max (?), ±S9)	□	7)
SCE	Don	Max (10-3M)	□	8)
SCE	Rat liver cell line	Max (?)	□	6)
SCE	CHO	Max (?)	□	9)
UDS	Rat hepatocytes	Max (?)	□	10)
MLA	L5178Y	Min ( 0.02 mg/ml)	○	1)
SM	Ch, hepatocites	Min ( 0.05 mg/ml)	○	1)
MNv	Mice (CD-1)	Max ( 2 g/kg, ip)	□	9, 11)
DLv	Mice	Max ( 2.5 g/kg, or )	□	12)
SLRLv	Drosophila	Max (?)	□	13)

１）Ministry of Labour, Japan: Mutagenicity Test Data of Exist. Chem. Subst., JETOC (Ed.) (1996) (Tables in English)
2) Ashby J., et al., (eds) Rep. IPCS, Progress in Mutation Res., , Vol. 5, 752 (1985)
3) Yoshikawa K., et al., Fd. Chem. Toxicol., 21, 221-223 (1983)
4) Zeiger E., et al., Environ. Mutagen., 7, 213-232 (1986)
5) Sofuni T. (Ed.): Data Book of Chromosomal Aberration Test In Vitro LIC, Tokyo (1998) (Tables in English)
6) Priston RAJ & Dean BJ,  Mutation Res., 5, 387-395 (1985)
7) Phillips et al., (1982)　(?)
8) Abe S & Sasaki M: J. Natl Cancer Inst., 58, 1635-1641 (1977)
9) Douglus RG, et al., Environ. Health Perspec., 65, 285-262 (1985)
10) Probst GS  & Hill LE, Prog. Mutation Res., 5, 387-395 (1985)
11) Morita T., et al: Mutation Res., 389, 3-122 (1997)
12) Hamano Y., et al., Osaka Pub. Health., Sanital Res. Cent., pp. 1-4 (1979)
13) Yoon JS., Environ Mutagen., 7, 349-367 (1985)

● 1, 2-Diethylhydrazine-HCl
　　　 7699-31-2　 Solvent　　　 161.08

AM

Sal.

Max ( 10 mg/plate, ±S9)

□

1)

１）Ministry of Labour, Japan: Mutagenicity Test Data of Exist. Chem. Subst., JETOC (Ed.) (1996) (in Japanese)

● Diethyl ketone （ジエチルケトン）
　　　 96-22-0　 Solvent　　　 86.13

YM

Yeast

( Aneuploid, Recombination, Gene mutation) Max (?) ( Gene conversion) Max (?)

○ ○

1) 2)

1) Zimmermann FK, et al,: Mutation Res., 149, 339-354 (1985)
2) Zimmermann FK, et al,: Mutation Res., 150, 203-210 (1985)

● Diechyl malonate (マロン酸ジエチル) (Malonic acid, diethylester; Diethyl propanedioate)
　　　 105-53-3　 Industryt　　　 160.17

AM

Sal./E.coli

Max ( 5.0 mg/plate, ±S9)

□

1)

１）Ministry of Labour, Japan: Japan Bioassay Res. Center, Ann. Rep. (2005) ;  Ministry of Labour, Japan: Mutagenicity Test Data of Exist. Chem. Subst., JETOC (Ed.), Suppl.4 (2008), p. 145 (Tables in English)

● Diethylnitrosamine (DEN) （ジエチルニトロサミン）
　　　 55-18-5　 Labouratory　　 102.14

DNA	E. coli	(DNA Repair); Min (1 μg/well)	○	1)
AM	Sal.	Min ( 60 μM, +S9)	○	2)
	Sal.	Min ( 0.02nM, +S9)	○w	3)
SLRL	Drosophila	Min (?)	○	4)
CA	CHL/IU	Min ( 3.0 mg/ml, +S9), 3-21h	○	5,6)
CA	CHO	Min ( 100 mM, +S9)	○	7)
SCE	CHO	Min ( 4.0 mM, +S9)	○	7)
SCE	Human LY	Max ( 500 μM, -S9)	□	8)
CA	V79/8AG	Min ( 10 mM, +S9)	○	9)
UDS	Rat/hepat.	Min ( 10-3 M)	○	10)
CT	BHK21c	Min (?)	○	11)
MNv	Rat/SD	Min ( 40 mg/kg, ip)	○	12)
MNv	Mice (NMRI)	Max( 2 x 100 mg/kg, ip)	□	13)
SCEv	CH	Max ( 200 mg/kg, ip)	□	14)

1) Ichinotsubo D, et al,: Mutation Res., 46, 53-62 (1977)
2) Yahagi T, et al,: Mutation Res., 48, 121 (1977)
3) McCann J., et al: Proc. Nt. Acad. Sci., USA, 72, 5135 (1975)
4) Fahmy OG, et al, Mutation Res., 3, 201-217 (1966)
4) Vogel E: In Montesano R, et al, (Eds): Screening Tests in Chemical Carcinogenesis,　IARC Sci., Pub. No. 12, 00. 117-137 (1976)
5) Matsuoka A, et al,: Mutation Res.,66, 277-290 (1979)
6) Sofuni T. (Ed.): Data Book of Chromosomal Aberration Test In Vitro LIC, Tokyo (1998) (Tables in English)
7) Natarajan AT, et al,: Mutation Res., 37, 83-90 (1976)
8) Craig-Holmes AP and Shaw MW: Mutation Res., 46-375-384 (1977)
9) Kuroki T, et al,: Cancer Res., 37, 1044-1050 (1977)
10) Williams GM & Laspia MF: Cancer Letter, 6, 199-206 (1979)
11) Styles JA: Br. J. Cance, 37, 931-936 (1978)
12) Trzos RJ, et al,: Mutation Res., 58, 79-86 (1978)
13) Wild D : Mutation Res., 56, 319-327 (1978)
13) Bayer U: Mutation Res., 56, 305-309 (1978)

● N, N'-Diethyl-p-phenilenediamine （N, N'-ジエチル-p-フェニレンジアミン）
　　　 93-05-0　 Industry 　 164.28

AM	Sal./ E. coli	Min (±S9) ?	○	1)
CA	CHL/IU	Min ( 0.0025　mg/ml, -Ｓ9), 24h; D20=0.009; TR=4800	◎	2)

1) Zeiger E, et al,: Environ. Mol. Mutagen, 11 (Suppl 12), 1-158 (1988)
2) Sofuni T, et al,: Mutation Res., 241, 175-213 (1990)

● O,O-Diethylphosphorochroridethioate
　　　 2524-04-1　 Industry　 188.61

AM

Sal.

Max ( 0.313 mg/plate, ±S9)

□

1)

１）Ministry of Labour, Japan: Mutagenicity Test Data of Exist. Chem. Subst., JETOC (Ed.), Suppl. 2 (2000) (Tables in English)

● Diethyl phthalate （フタル酸ジエチル；DEP）
　　　 84-66-2　 Industry　 222.23

AM	Sal./ E. coli	Max (±S9) ?	□	1)
CA	CHL/IU	Max ( 0.25 mg/ml, -Ｓ9), 24-48h; (No data for +S9)	□	2, 3)

1) Yoshikawa K., et al., Fd Chem. Toxic., 21, 221-223 (1983)
2) Ishidate MJr. & Odashima S.: Mutation Res., 48, 337-354 (1977)
3) Sofuni T. (Ed.): Data Book of Chromosomal Aberration Test In Vitro LIC, Tokyo (1998) (Tables in English)

US-NTP Genotoxicity Screening：
○ AmesTest： □
○ CA Test with CHO Cells：　□　
○ SCE Test with CHO Cells：　○

【Note】　(Cited from CICADs Documents,1, 1998))

A comparison of the results of in vitro mutagenic assays of diethyl phthalate in various strains of Salmonella typhimurium shows contradictory findings. Diethyl phthalate has been shown to be mutagenic for S. typhimurium strains TA100 and TA1535 only without metabolic activation (Kozumbo et al., 1982; Agarwal et al., 1985). The maximum ratios of induced revertants to control were about 2?3 (Kozumbo et al., 1982; Agarwal et al., 1985) and about 2 (Agarwal et al., 1985) for TA100 and TA1535, respectively. No induced revertants were observed for TA98 and TA1537 with or without metabolic activation (Rubin et al., 1979; Agarwal et al., 1985).     Contrary to positive findings, diethyl phthalate has been found to be non-mutagenic in S. typhimurium strains TA98, TA100, TA1535, and TA1537 with or without metabolic activation (Zeiger et al., 1982, 1985; NTP, 1995).    Two chromosomal aberration assays with Chinese hamster fibroblasts and ovaries, respectively, produced negative results for diethyl phthalate at concentrations up to 0.324 mg/ml (Ishidate & Odashima, 1977; NTP, 1995). However, at culture concentrations of 0.05, 0.167, and 0.5 μg/litre, diethyl phthalate produced a concentration-related increase in the number of relative sister chromatid exchanges per chromosome. This effect occurred only in the presence of the S9 fraction from rat liver homogenates (NTP, 1995).    In summary, the results of in vitro mutagenicity tests in microbial assays are equivocal. No in vivo studies were located. References ・Agarwal DK, Lawrence WH, Nunez LJ, Autian J (1985) Mutagenicity evaluation of phthalic acid esters and metabolites in Salmonellatyphimurium cultures. Journal of Toxicology and Environmental Health, 16(1): 61-69. ・Ishidate M Jr, Odashima S (1977) Chromosome tests with 134 compounds on Chinese hamster cells in vitro: A screening for chemical carcinogens. Mutation Research, 48: 337-354. ・Kozumbo WJ, Kroll R, Rubin RJ (1982) Assessment of the mutagenicity of phthalate esters. Environmental Health Perspectives, 45: 103-109. ; ・NTP (1995) NTP technical report on the toxicology and carcinogenesis studies of diethylphthalate (CAS No. 84-66-2) in F344/N rats and B6C3F1 mice (dermal studies) with dermal initiation/promotion study of diethylphthalate and dimethylphthalate (CAS No. 131-11-3) in male Swiss (CD-1) mice. Research Triangle Park, NC, US Department of Health and Human Services, National Institutes of Health, National Toxicology Program (NTP TR 429). ・Rubin RJ, Kozumbo W, Kroll R (1979) Ames mutagenic assay of a series of phthalate esters: Positive response of dimethyl and diethyl esters. Toxicology and Applied Pharmacology, 48: A133. ・Zeiger E, Haworth E, Speck S, Mortelmans K (1982) Phthalate ester testing in the National Toxicology Program’s environmental mutagenesis test development program. Environmental Health Perspectives, 45:99?101. ・Zeiger E, Haworth S, Mortelmans K, Speck W (1985) Mutagenicity testing of di(2-ethylhexyl) phthalate and related chemicals in Salmonella. Environmental Mutagenesis, 7: 213-232.

● Diethylstilbestrol (ジエチルスチルベステロール）
　　 56-53-1　Medicine　 268.34

AM	Sal.	Max ( ?)	□	1-4)
YM	S. cerevisiae	(Aneuploid) Min (?)	○	5)
CA	CH	Poly Min (?)	○	6)
CA	CHL/IU	Min (0.0075 mg/ml, -S9), 48h ; PD20=0.0074 (Poly)	○	7,8)
CA	Human LY	Min (?)	○	9)
SCE	Don	Max ( ?)	□	10)
SCE	Human LY	Min (?)	○	11)
MLA	L5178Y	Min (?)	○	12)
MNv	Mice/BM	Max (?)	□	13)
CAv	Mice/BM	Min (?) (Negative for SCE)	○	14)
CT	C3H/10T1/2	Max (?)(±S9)	□	15)

1) McCann J., et al. : Proc. Natl Acad. Sci. (USA), 72,　5135-5139 (1975)
2) Dunkel VC,: J. Assoc. off. Anal. Chem., 62, 874-882 (1979)
3) Anderson D & Styles JA: Br. J. Cancer, 37, 924-930 (1978)
4) Kawachi T, et al,: in: The Predictive Value of Short-Term Screening Tests in Carcinogenicity Evaluation,(Eds):
　　Williams GM et al., Appl. Methods Oncol., 3, 253-267 (1980)
5) Parry JM, et al,: Nature (London), 294, 263-265 (1981)
6) Sawada M & Ishidate MJr: Mutation Res., 57, 175-182 (1978)
7) Ishidate MJr, et al,: Jap. Cancer Res.(GANN), Monogr., 27, 95-108 (1981)
8) Sofuni T, (Ed.): Data Book of Chromosomal Aberration Test In Vitro, LIC, Tokyo (1998) (Tables in English)
9) Dzangulashvili NA: Cytol. Genet. (USSR), 16(2), 28-33(1982)
10) Abe S & Sasaki M: J. Natl Cancer Inst., 58, 1635-1641 (1977)
11) Hill A & Wolff S: Cancer Res., 43, 4114-4118 (1982)
12) Clive D, et al,: Mutation Res., 59,-61-108 (1979)
13) Chrisman CL & Baumgartner, Mutation Res., 67, 157-160 (1979)
14) Ivett JL and Tice RR: Environ. Mutagen., 3, 445-452 (1981)
15) Lillehaug JR & Djurhuus R: Carcinogenesis, 3, 797-799 (1982)

【Note】 (Cited from IARC Monograph, Suppl. 6, 1987)

No data were available on the genetic and related effects of DES. 　　DES induced CAs in bone-marrow cells of mice treated in vivo, but data on induction of SCE and MNs were equivocal; it induced SCEs in one study in hamsters with DES (Liehr, Avitts, Randerath, 5301, 1986). Aneuploidy was induced in human cells in vitro, but data on induction of SCEs, CA and mutation were inconclusive; it induced DNA strand breaks, but not UDS, except in a single study. Tests for transformation in rat and Syrian hamster embryo cells gave positive results, while results fro mouse cells were negative. Aneuploidy and DNA strand breaks were induced in rodent cell in vitro, but results for CAs, MNs and SCEs were equivocal; DES did not induce mutation or UDS, except in a single study in Syrian hamster embryo cells. It did not inhibit intercellular communication of Chinese hamster V78 cells. It induced aneuploidy in fungi, but , in most studies, it did not induce mutation, recombination or gene conversion. It did not induce mutation in a variety of bacterial and insect systems, but it was mutagenic in plants. DNA damage was not induced in fungi or bacteria. DES induced single-strand breaks in bacteriophage DNA in the presence of a horseradish peroxidase activation system.

● Diethyl sulfate （硫酸ジエチル）
　　　 64-67-5　Industry 154.19

AM	Sal./ E. coli	Min ( 0.313/plate, ±S9); spa= 9640 (TA100)	◎	1)
AM	Sal..	Min (?)	○	2)
CA	CHL/IU	Min ( 0.63 mg/ml, -Ｓ9), 24h ; D20= 0.28	○	1)
CA	CHO	Min (?)	○	2)
SCE	CHO	Min (?)	○	2)
MN	Mamal. cells	Min (?)	○	2)
SM	Mamal. cells	Min (?)	○	2)
UDS	Hum. cells	Min (?)	○	2)
DLs	Mice	Min (?)	○	2)
SLRLv	Drosophila	Min (?)	○	2)

１） Ministry of Labour, Japan: Mutagenicity Test Data of Exist. Chem. Subst., JETOC (Ed.) (1996) (Tables in English)
2) Hazardous Substances Data Bank (HSDH), US National Library of Medicine (1996)

● Diflubenzuron 　（ジフルベンズロン）
　　　 35367-38-5　Insecticide 310.7

REC	B. subtilis	Max ( 2.0 mg/disk)	□	1)
AM	Sal./E. coli	Max ( 5.0 mg/plate, ±S9)	□	1)
CA	CHO	Max ( 0.25 mg/ml, ±S9)	□	1)
MN	Mice	Max ( 1.5 g/kg x 2)	□	1)

１） Agro Kane-Sho, Co. Ltd.: J. Pesticide Sci., 17, S159-S164 (1992) (in Japanese)

● Difluoromethane
　　　　 75-37-6　Industry　 66.05

AM

Sal./ E. coli

Max ( 44%, ±S9) ( in vapor)

□

1)

１） Ministry of Labour, Japan: Mutagenicity Test Data of Exist. Chem. Subst., JETOC (Ed.) (1996) (Tables in English)

● Diglycidyl ether　（ジグリシジルエーテル； DGE）
　　 2238-07-5　Industry　 130.14

AM	Sal.	Min (?)	○	1,2)
MB	Bact. phages	Min (?)	○	1,2)
MB	N. crassa (アカパンカ)	Min (?)	○	1,2)
CA	Vicia faba; (ソラマメ)	Min (?)	○	1,2)

１）Hine CH., et al.: Patty's Industrail Hygiene and Toxicology, 3rd Rev. Ed., Bol. 2A, Toxicology, pp. 2204-2208, Clayton GD. & Clayton FE (Eds.), John Wiley & Sons, New York (1981)
2) Berufsgenossenschaft der Chemischen Industrie: Toxicological Evaluations No. 66. BG Chemie,　Heidelberg, FRG (Sept., 1989)

● Diheptyl phthalate 　（フタル酸ジヘプチルエステル）
　　　　 3648-21-3 　Industry　　 362.51

AM	Sal./ E. coli	Max ( 5.0 mg/plate,±S9)	□	1)
CA	CHL/IU	Max ( 5.0 mg/ml, -Ｓ9), 6-18h; (No data for +S9)	□	1)
CA	CHL/IU	Max ( 4.0 mg/ml, ±Ｓ9), 6-18h;	□	2)

1) Ministry of Health, Labour & Welfare, Japan (Ed): Toxicity Testing Reports of Environ. Chemicals, Vol. 4 (1996) (Tables in  English)
2) Sofuni T, (Ed.): Data Book of Chromosomal Aberration Test In Vitro LIC, Tokyo (1998) (Tables in English)

●Top Page　（トップページ）

●Abbreviation 　（省略記号）

●Mutagenicity （変異原性）

●Test Systems　(試験法の種類）

●Technical Problems　（技術的問題点）

●List of　Compounds（化合物リスト）

●Evaluation of Results　（試験結果の評価）