111111111111111111111111111111111111111111111111111111111111 • 

OTS0522942 

One Source. One Search. One Solution. 

AMES TEST WITH HEXABROMIDES WITH COVER 

LETTER DATED 031290 

24 APR 1978 

U.R Department of Commerce 

National Technical Information Service 
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COOING FORM FOR SRC INDEXING REVISED 10/1.5/86 c 

0180522942 

AMES TEST WITH HEXABRDMIDES WITH COVER LETTER DATED 031290 

:. 

HEXABRDMOCYCLODODECANE (3194-55-6) 

• 
1'3ASF' Corporation · 

'-f..il'rt:if ied Mail 

Return Receipt Requested i?f-9hD DD'? j,(!; ~ . . 

March 12, 1990 ~=~e.>QBQsS #P?; 

Attention: B(dl Health & Safety Reporting Rule Notification · u. is. Environmental Protection Agency 

Document Precessing Center (TS-790) 

Office of Toxic substances 

401 M street, SW 

washington, DC 20460 

Ladies and Gentlemen: 

SubJect: Health & Safety Study Reporting 

54 Federal Register 51114, December 12, 1989 

25th ITC Report 

In response to the TSCA reporting rule referenced above, BASF 

Corporation is submitting the attached studies on: 

CAS Reg. No. 

1163-19-5 

3194-55-6 

32534-81-9 

32536-52-0 

DECABROMODIPHENYLETHER 

Name 

Decabrornodiphenyl Ether 

Hexabrornocyclcdodecane 

Pentabromodiphenyl Ether 

octabrornodiphenyl Ether .. CAS REG. NO. 1163-19-5 

1. Bericht uber Versucbe zur Ermittlung der rnittler~n todlicheri 

Dosen fun£ verschiedener Verbindungen, 10.03.1976 · · 

2. Ames Metabolic Activation Test to Assess the Potential 

Mutagenic Effect of Brornkal 82-0 DE, 08.02.3:978 · 

3. Ames Metabolic Activation Test to Assess the Potential · ..Mutagenic Effect of Muster 83, 17.10.1984 · 

4. Ames Metabolic Activation Test to Assess the :pqtential 

Mutagenic Effect of Muster 88, 16.10.1984; 

5. Final Report. 14-Day Repeated Dose Feeding study - MiCe, 

13 .1.1.1978 

6. Final Report. 14-Day Repeated Do.se Feec'iing Study '- R.ats, 

14.11.1978 

7. 90-Day Subcbronic Feeding Study ~lli Rats on Decabromodiphenyl 

Oxide, 27.07.1979 · .. . •;:. 

1609 Bi::fd& Avenue_ Wyandone. MiChigan 48192 r.313J 246-fnoo -.' . . . . : . -~ . 
Page 2 

u. s. Envir~nmental Protection Agency 

DECABROMODIPHENYLETHER CAS REG. NO. 1163-19~5 (Cont.) . . . . . . " . ··. . . ,, .. ~ ' ' .· 

8. 90-Day Subchronic Feeding study in Rats on Decabromodiphenyl 

Oxide, 27.07.1979 · 

9. Results of 30-Day Rat Dietary Feeding studies on Octabrom6-

biphenyl SA-1902 and Decabromodiphenyl Oxide SA-1892.1, 

28.01.1971 

10; Ergebnisbericht uber Untersuchungen zur Bildung von Polybromdibenzofuranen und -dioxinen wahrend der Extrusion von 

Polybutandiol-terephthalat (PBTPl; Flamrnschutzmittel: Decabromodiphenylether 

·;,··. 

11. Untersuchung zur Bildung von Pol.ybrom-dibenzofuranen und ,., dioxinen bei der Extrusion von Poly-Butanediol-terephthalat 

(PBTP); Flammschutzmittel: Decabrom-diphenyiether; Teil 21 

Produktionsanlage 

HEXABRO~!OCYCLODODECANE CAS REG. NO. 3194-55-6 

1. Prufungsbericht uber die toxikclogischen Untersuchungen mit 

Hexabromocyclododecan der Firma Chemische Fabrik Kalk GmbH, 

Koln-Kalk an Laboratoriwnstieren, 04.10.1971. 

2. Bericht uber die Prufung der akuten Toxizitat an der Goldorfe (Leuciscus idus L., Goldvariante), 18.03.1988 

3. Ames Test for Hexabromid s, 24.04.1978 

4. Hexabromocyclododecane: 28-day feeding trials with rats 

(with Germany summary - 17.11.1.969) 

s. Hexabromocyclododecant 90-day feeding trials with rats (with 

Germany summary 04.02.1970) 

6. Report on the study of the irritation of Hexabromocyclodo- " 

decane to the dorsal skin of rabbits after 20,..hour exPosure, 

04.10.1962 

7. Report on the. study of the. primary irritation of Hexabromocyclododecane to the eye'.of rabbits, 04.1.0.1962 · 

B. Report on the study of the acute oral toxicity of Heltabr.,:;mo'i: 

cyclododecane in the mouse, 04.10.1962 · · · · · · 

9. Notiz: ALD 50, Ratte, oral, 28.11.1962 

10. Ames metabolic activation tes.t to assess j:he pqtential 

mutagenic effect of compound No. !19, 19~'09;1978 

·''. 

; .. 
Page 3 .. ., <'. 

u. s. Environmental Protection Agency - '.,..·· 

HEXABROMOCYCLODODECANE CAS REG. NO. 3194"'55-6 CCont:) .··. . . . . ' 

11. Migrat;ion von HBCD aus geschailintem Polystyrol, 27;06.~3 

12. Migration von Flarnmschutzrnitteln aus"gescha\.Untern Polyst:Yrol 08.08.85, 19.12.85, 28.08.86 .. 

13. APME: Expandable Polystyrene Information Dossier, p 18 with 

Data to Aquatic toxicity and Bioaccurnulation (log Pow a.o.), 

March 1988 · · 

14. 

15. 

16. 

17. 

Al.gal Growth Inhibition Test, 1990/01/31 

Determination of the acute toxicity of Hexabromid s.-to the 

waterflea Daphnia magna Strails, 1990/01/30 . U 

oxygen consumption Test (using Pseudomonas putida by the 

test method of Robra), 1989/04/19 -

Biologische Abbau Tests, 1980/05/06, 1981/10/16 

PENTABROMODIPHENYLETHER CAS REG. NO. 32534-81-9 

1. Prufung der akuten Toxizitat au der Gol.dorfe, 13.02.1984 

2. Toxicologische Prll.fung veri Penta-brom-diphenylaether 

3. Prufung von Bromkal 70-5 DE im Augenreiztest am Kaninchen; 

January 1981 

4. Prufung von Bromkal 70-5 DE irn Hautreiztest·am Kaninchen, 

January 1981 

5. Ames metabolic activation test to assess the potential 

mutagenic effect of Bromkal 70-5 DE, 08.02.1978 

t• OCTABROMOD!PHENYLETHER CAS REG. NO •. 32536-52-0 

l. Be:richt uber ve_rsuche zu:r E:rmittlung der ve:rt:rag1ichkeit 'lion·. 

Brornkal 82-0DE-Ruckstand, Bromkal 79-8DE~nied:rigschmelzend 

und Brornkal 79-8DE-Ruckstand,''04.09.1984 · , . 

2. Ames metabolic activation test to .assess the potential 

3. 

mutagenic effect of Muster 84; 12."10;1984 · · · 

Ames metabolic activation test 

mutagenic effect of Muster 8z"i 

to a.Sse_ss i:pe ,potential 30.10;1984 • . .•. - : 

·. •'::; 

i .. ·· 

.. ·' 

''··· ·-~- . 
!?age 4 , U. ·S. Environmental Protection Agency 

OCTABROMODil?HENYLETHER CAS REG. NO. 32536-52-0 

4. Ames metabolic activation test to assess the potential mutagenic effect of Muster 13, 15.05.1978 

5. l?rufung von Bromkal 79-8 DE im Augenreiztest am Kaninchen, June 1980 

6. Prufung von Bromkal 79-B DE im Hautreiztest ,am Kahinchen, June 1980 

7. Bericht uber Versuche zur Ermittlung der mittleren todlichen 

Dosen funf verschiedener Verbindungen, 10.03.1976 

B. Bericht uber Versuche zur Ermittlung der mittleren todlichen 

Oasis van Bromkal 79-8 DE, 21.05.1976 

submitting site: BASF Corporation 

8 campus Drive 

Parsippany, NJ 07054 

Stmmitting Official: Roberta A. Hurley Sr. Product Regulations Specialist BASF corporation ., 1609 Biddle Avenue ' 

Wyandotte, MI 48192-3799 

Telephone: ( 313) 246-6214 

!?lease contact me at 313-246-6214 if you have any questions. 

mk 

Enc. 

Very truly yours, 

BASF CORPORATION 

Roberta 

v?~A~J:·· A. Hurley Sr' Prodt1ct Regulatio. specialist 

\: 

,, 
' Prrt F. O:~nh . 

VorS!i!hcr <isr AM, l:lolo!iUlm~!mrm~l~_olo_nte 

P' t~a. ·m~''"''"' <!, ............ .i··-'···" :.... l·.ts'itut • • r.~r tl:m•ers:tut n~ ... "'" 7:th~ ~ :vl .. ~r t:ru~e J7 

'D·' 6 :.·. :·,:l ' ,, ~ '1 •t ..,. 8 R D • I •' I" • '•\ I -•1 

lelo!on (0 ;;i :JlJ ;g :n :s, 19 a1 aa, 19 S172 

AMES TEST 

FOR 

HEXABROMID S 

;:.-. 

'· 10 ~r-·1 t..· r_ . . 

... ~- >~~) 

. ,;:.;;,.;;...;:~:.: ,. 

.•--'&o:'EPA.;OTB··· 

· 11\IIIIBIIIII [100.b&~~-S2X _ 

'l?(;.~o'Q;0o 319 · 
C,ommon name: Hexabromid s 

Chemi~al name: 1.2,5,6,9.10-Hexabromocyclododecane 

Chemical structure: ,-(CH2-CH2-CH-CH)---

, !r ~r ,;( 

I J 

L . .,------,----i 

Number of compound: 78/155 

Solubility: water: insoluble 

ethanole: 2 % 

Lutrol < 2 % 

Degree of purity: - 95 % 

'-·· 
I 

! ·. 

lNTRODUC'TIO!'l 

The A11es test (1,2) is a short term test for the. detection. of carcinogens usirig 

mutagen icily in bacteria OS endpoint. The test considers inilmmalio~ metabolism by 

the use of liver homogenate, A high, but. not complete qualitative correlation wad 

found between carcinogenicity and mutagenicity in the A'fles test. McCann and 

A'fles {3) found that 90 % of the "knowll animal or humal' carcinogens" were pos.itive1 93 % of the "putative non-ccrcint;Jgens11 were negative in the Ames t~st .. 

In the knes test the effect of the test compound is investigated upon the number of 

backmutations in a battery of histidine auxotrophic Salmonella typhirrurium mutants ,, to histidine prototrophy (2,5,6). The strain TA 100 is derived froll)}histidine proto• 

trophic bacteria by a substitution mutation, the strgins TA 1537 and TA 98 by fro- . ' . 

meshift mutations. All three strains lack the DNA excision repair system {uvrB) and 

show a strong reduction in the hydrophilic polysoccoride Ioyer (rfa) which facilitates the penetration of lipophilic compounds into tho bacteria. TA 98 and TA 100 

possess a modified postreplicofion DNA repair system which 0i'ncreases the rate of mutations by error prone repair {6). 

Since mast carcinogens ore not carcinogenic themselves, but only after metabolism (7), 

lhe compounds are tested in the Ames test not only directly, but also in the presence 

of a mammalian m•tabolizing system. 10,000 g supernatant of liver homogenate from 

rots treated with Aroclor 1254 and a NADPH generating system were shown to be ve1y .. 

favourable for oc:tivation {2). The liver represents the most im;>ortant organ for metabolism of foreign compounds and. several drug m~tobolizing enzymas are induced by 

Aroclor {8). 

Aromatic and olefinic compounds can be mo>tabolized to epoxides (9~ llJ: Epoxidcs ., 

are aften mutagens. Mnn}' 

jugation with glutathione. 

cpaxldes are inactivated by epoxid_e hydr~tase ?r by .con-, .. 

i, 1, 1-Trishloroproperic 2,3.~oxide inhibits the epoxidli .··. 

hydratase and depletes glutcthia!)e. 'Therefore, its use in ithe, liv.er homogeiu,te :'i)ledii:i_ted 

'!.i. .. ~ . '!" .... · .. 
- .;~2 

mulogenicity test con increase the sensitivity of the test and at the' some tim·! may, 

gi;,.c .information about the route of the oCtivctioJ·: Such information is voluabie, 

since minor modifications of the compound can ~comple>tely alter tlie rri~tobolism, 

In this screening te5t mutagenicity was studied with S, typhimurium TA 98, 

TA 100 and TA 1537. The compound was tested in the presence end absence of en , ... 

activating system. An epoxide hydratase inhibitor end glutoth.ione depleting agent was 

aiso used in some experiments. 

'.,. 

,, 

.. .:.': 

.. ·· 
• 

3 .. 

MATERIAL AND METHODS 

Chemicals 

;;. -. 

The test compounds were stored at 4 °C in the dark aiid dissolved in diinethylsulf- " rl 

oxide (DMSO) or water on the dey of the mutagenicity experiment. 

Tissue preparations 

Mole Sprague Dawley rots (200 - 300 g) received a single intraperiionecil injection - . :l 

of Aroclor 1254 (500 mg/kg body weight; Aroclor wos dilu,ted with sun flower oil' 

1 : 5 v/v) 6 days before sacrifice, The liver was homogenized in three volumes , 

of sterile, cold KCI (150 mM, buffered with No phO.phate at pH 7.4). The homogenate wos centrifuged at 10,000 g for 10 minutes. One volume c;>f the resulting 

supernatant was mixed with one volume 24 mM Mi!C12

-100 mM KCI and one voluma 

12 mM NADP-15 mM glucose-6-phosphate-150 mM No phosphate pH 7.4. This 

preparation is termed S-9 Mix. For all experim:nts fresh tissue preparations were 

used fi'om animals which w~re sacrificed on the day of the experiment. 

Bacteria 

Bacteria ware grown over night in nutrient broth (8 g Bacfo t-.iufri<int Oroth (DIFCO)' 

+ 5 g NaCI/Iiter). For inoculation stock cultures which were stored at .;.70°C were 

used. Before the expcrim·3nt, bacteria were centrifuged and resuspended' in resusp\"n~ 

sion medium (1.6 g Bacto Nutrient Broth + 5g NaCI/Iiter) and adji.JStecl to q titer , 

.. . , 

of 1.7 r. 109 bacteria (colony forming units) par mill'iliter detormincid by ne~htilom•lry ,. 

'_;,. 
~·· 4 -

• 

MJtogenicity experiinents 

· .. The mutagenicity experimenh; were performed as described by Ames (2) with minor modi-

. fication. The test compound, 500 pi S-9 Mix (or.SOO pi 150 mM KCI), 100 pi of the 

bacterial suspension and 2000 pi tap agar (0.55 % agar, 0,55 % NaCI, 50 f'M histidine, 

~0 pM biotin, 25 mM No phosphate pH 7 .4, 45° C) were mixed in a fest tube and 

poured onto a petridish with minimal agar.(l.5% agar, Vogel-Bonner E medium (13) 

with 2% glucose). Wnere indicated the epoxide hydratase inhibitor and glutathione 

depl~tor 1, 1, 1-trichloropropene 2,3-oxide (TCPO) was added (0.3 pi per plate) in 10 pi 

DMSO. Corresponding plates without TCPO ~eceived 10 fl DMSO. After incubction for 

3 days in the dark, colonies (his+ revertants) were counted. The person who performed 

'the counting did not know the specifications of the plates . 

• 

Evdry single experiment contained posilive controls for checking the activity of the" metabolizing system and the mutability of the bacteria os well as negative controls in the 

form of sterility controls and incubations without test compound, 
• 

- ::J -

RESULTS AND DISCUSSION 

Controls 

,, 

Control plates without mutagen showed numbers of spontaneous revertant colonies per 

plate similar to those described by Ames (2), As positive controls N.,methyi·:N' -nitrcN-nitrosoguanidine and benzo(a)pyrene 4,5-oxide were used in the experimel)ts fer direct mutagenicity and 3-methylchalanthrene, benzo(a)pyrene and 2-aminoanthracene in 

the experiments with an activating system, Benza(a)pyrene is ai:tivat!ld. well by liver· 

preparations from 3-me!hylcholaillhr<ine treated rats, but only poorly by preparations 

(. from phenobarbital treated rats. The reverse is !rue for 3-methylcholcnthrene (2), keeler 1254 induces monooxygenoses which are induced by phenobarbital as well' as monooxygenoses which are induced by 3-methylcholanthrene (8). Both Benzo(a)pyrene and 

3-methylcholanthrene were activated in our experiments. ·This indicates that both me• 

labolizing systems were functioning; 

, .. 

Hexabromid S 

Hexabromid S was tested for mutagenicity with Salmonella typhimuriun;', TA 100, TA 1537 

and TA 98, '· In the presence of S-9 Mix, seven different doses from 3.15 to 3000 pg per 

plate were used, in its absence five doses fro:n 31.5 'to 3000 pg. No mutagenicity was 

observed under_ all these conditions. But hexabromid S precipitated at doses:;. lOOD.pg, 

which reduces the sensitivity of the lest. This limitation is not very severe since most 

of the carcinogens tested by M:Cann el al. (3) were mutagonic at lower doses, 

Furthermore in some experiments wlth TA 98, on epoxide hydratase inhibiior and 

glutathione depletor, 1, I, 1-trichloropropene 2, 3-oxide w'iis added to the S-9 Mix in 

order to increase the sensitivity of the lest towards ccmpoimdS whicfl.are oclivatecl lo . . . . .. ·. 

mutagenic epoxides. ·Also under this condition no mutagenic;ity was o-Bserved with 

hexabromid S. 

~.: 

.. :~' .. ·:· .. ' ·?.0-. ~/ ;fl .. . , • . , -' c:h-,,.;c-t} . . . 

. . ... . .. .. . •. . . . . . ...... . Mainz, April 19, 1978 

. :: ... ' . 

;:: 
• 

( 

( 

• 

AMES lEST for Hcxobrcmid 5 

WITH 5~9 MIX (fran liver homogenol~ of Aroelor 1254 treated rob) 

Dosll 4's/ple~to) Solvent TA 100 (pi DMSO) 

0 10 185 

0 10 167 176 

3 15 10 150 186 

10 10 175 165 

3LS 10 M9 164 

100 10 170 180 

315 10 139 204 

1000§ 10 175. 174 

3000§ 30 158 139 

10 tlcn~o(o)pynme 10 1~00 1580 

10 2-Aminocnthror:.enc 10 4600 4800 

90 3-Mcthylr:.hcl!oothrene !lO 3600 4000 

WITHOUT S-9 MIX 

Dose {pg/plotc) Sol11cnt TA 100 (VI DM~D~ 

0 10 187 161 

0 10 187 183 

31.5 10 149 101 

100 10 177 182 

315 10 186 175 

1000§ 10 184 176 

3000§ 30 170 213 

1 Bcn;:o(a)pyrenc 10 1060 1230 

4,5-oxldc 

10 N~Methyi-N' ···nifro-N- 10 70000 64000 

nitrosoguonidinc 

SUI..\VJ:.St!ZEO RESULTS: Hexobromld S 

did not 'how crt)- mutc:gcnic: cffCct under, 

ell expo-rimenfal c~dilicns. 

TA 1537 TA 98 TA 98, TCt' 

1o 25 55 56 74 53, 

33 22 64 68 57 72 

c 

32 18 65 56 63 72 

38 18 55 66 71 60 

39 29 58 41 69 54 

24 32 58 51 70 57 

28 78 74 68 70 

30 22 60 50 59 59 

28 35 76 <:<;· 60 61 

267 268 830 1250 1070 1080 

175 174 470!) 5600 5500 5300 

129 139 1510 1610 1510 

TA 1537 TA 98 

12 14 32 42 

10 13 37 22 

9 II 40 44 

10 7 4C 36 

14 4 30 35 

11 10 29 40 

11 8 < 49 35 

506 467 iS8.2:.>40 

ISO 158 92 67 

lhc canpounds ~re les;tcd for mufogcnicity OS described by Ames e, ol" (Mut. Res. 31 (1975) .. ~47~64) wilh Only mininial madifJcotloru 

(see "M'llerials ond Mi1hads"), Atldttlonally, on cpoxlde h~drolas.c inhibitor end glulathioRe depl~lor~ l,_f:i;;,J{chlolopropcne oxide·.~ 

used (see cohunn h~odcd "T,6, 99, TCPO")" The tohles 1how tho i1umbc:r of hisT fc~rtcnt colo~~~' or. tndiv!d~l ~)Ctcs. . . . 

DMSO: Dimalhylsulfoxide. ' -- .. .. --: - . ....~.: 

§) Proc:ipitotion of Jest compound on lhc plate, 

. ·.~ .," ' 

. '~ 
. 

.. ' 

( 

( 

- 6 -

REFERENCES 

l. Ames, B. N.; Dur·ston, W. W.; Yamasaki, E.; lee, F. D.: '7-Corcinogens 

ore mutagens: A simple test system combining liver homogenates for activation 

and bacteria for detection. Proc. Nat. Aced. Sci. USA 70 (1973) 2281-2285. 

2. Pmes, B. N.; McCann, J.; Yamasaki, E.: M"thods for detecting carcinog.,ns 

and mutagens with the Solmonello/mammalian-micrasome mutagenicity test. Mut. 

Res. 31 (1975) 347-364. 

3. 

4. 

5. 

McConn, J.; Ames, B. N.: Detection of carcinogens as mutagens in the 

Salmonella/microsome test: .A.soy of 300 chemicals. Proc. Not. Aced. Sci. 

USA 72 (1975) 5135-5139. 

Purchase, I. F. H.; Longstaff, E.; .A.hby, J.; Styles, J; A.; Anderson, D.; 

Lefevre, P. A.; Westwood, F. R.: Evaluation of six short term test; for detectfng organic chemiccf carcinogens and recommendations for their use. 

Nature 264 (1976) 624-627, 

Ames, B. N .; L.ee, F. D,; Durston, W, E.: An improved bacterial test 

system for the detection and classification of mutagens and carcinogens. Proc. 

Nat, Acc:id. Sci. USA 70 {1973) 782-786. 

6, McCann, J.; Spingarn, N. E.; Kobori, J.; Ames, B. N.: Detection of 

carcinogens as mutagens: Bacterial tester strains with R factor plosmids. Proc. 

Nat, Aced, Set. USA 72 {1975) 979-983. 

7. Miller, J, A.; Miller, E. C.; Some cur;rent threshblds of resec;rch ir; chemical carcinogenesis. In: P. 0. P. Ts' 0 and J. A. Dil'aolo (eds.): ChamicCII 

carcinogenesis, Part B, pp 61..:85, Marcel Bekker Inc.; Naw York (1974). . . 

... -· ... 
- 7 -: 

8. Alvares, A. P.; Bickers, D. R.; Kappas, A.: Polychlorinated biphenyls: 

A new type of inducer of cytochrome P-443 in the liver. Proc •. Nat. Aced. 

Sci. USA 70 (1973) 1321-1325. 

9. Daly, J. W.; Jerin~· .. D. M.; Witkop, B.: Arene oxides end the NIH shift: 

!he m"tabolism, toxicity end carcinogenicity of aromatic compounds. Experientia 

28 (1972) 1129-1149. 

10. O•osch, F.: Mammalian epoxide hydrases: Inducible enzymes catalyzing the inactive~ 

tion of carcinogenic and cytotoxic metabolites derived from aromatic and olefinic 

compounds. Xenobiotico 3 (1973) 305-340. 

11. Sims, P.; Grover, P. L.: Epoxides in polycyclic aromatic hyclrocarbon metabolism and carcinogenesis. Adv. Cancer nes. 20 (1974) 166-274 •.. 

12. Glatt, H. R.; O•;sch, F.; Frigerio, A.; Gorattini, S.: Epoxides metabolically 

produced from som• known corcinogons and from some clinically used drugs. 

I. Differences in carcinogenicity. Int. ~. Cancer 16 (1975) 787-797. 

13. Vogel, H. J.; Bonner, D. M.: Acetylornith~,; of E. coli: Portio! purification onil some properties • .J. Bioi. Chern. 218 (1956) 97"'106. 

·. :··. 

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