111111111111111111111111111111111111111111111111111111111111 

# • OTS0522942 One Source. One Search. OneSolution. 

# AMES TEST WITH HEXABROMIDES WITH COVER LETTER DATED 031290

24 APR 1978

U.R Departmentof Commerce 

### NationalTechnical InformationService

# One Source. One Search. One Solution.

Providing Permanent, Easy Access to U.S. Government Information



## The National Technical Information Service isthe Nation's largest repositoryand disseminatorof government-initiated scientific, technical, engineering, and related business information. The NTIS collection includes almost 3million information products in a variety offormats: electronic download, online access, DVD, CD-ROM, magnetictape, diskette, multimedia, microfiche and paper. Search the NTIS Database from 1990 forward 

### More than 600,000 government research information products have been added to the NTIS collection since 1990. All bibliographic entries for those products are searchable on the NTIS Web site at www ntis gov. Download Publications (1997 • Present) 

### NTIS provides the full text of many reports received since 1997 as downloadable PDF files. When an agency stops maintaining areport on its Web site, NTIS still offers adownloadable version. There is afee for each download of most publications. 

### Formore informationvisitourwebsite: 

# www.ntis.gov 

# /S_;i'- U.S. DEPARTMENTOFCOMMERCE 

# .

**~·.-** 

# 't: TechnologyAdministration \ · / NationalTechnical Information Service ..,_.,. Springfield,VA 22161

### COOING FORM FORSRC 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:ified Mail

Return Receipt Requested 

## i?f-9hDDD'?

# 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 Mstreet, 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. MiChigan48192 r.313J246-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



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

\: 

## ,,

### ' PrrtF.



### O:~nh . 

### VorS!i!hcr <isr AM,



### l:lolo!iUlm~!mrm~l~_olo_nte P

'

**·m~''"''"'** .i··-'···" 

### l·.ts'itut

**r.~r** 

### tl:m•ers:tut

**t~a.** <!,............:.... • •

**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

## a1aa, 19S172



### AMES TEST FOR HEXABROMID S ;:.-. 

# '·

**~r-·1**t..·

r_ . . 10 ...

**~- >~~)** 

.

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

### .•--'&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 mutagenicily 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 0 i'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 inithe,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 3000pg. 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.

·. :··.

# ....

**~** 

# z 

# - u. ILl 

# a:

**~** 

# "' ILl 

# .... 

# = .... 

# ...

**~** 

### National Technical Information Service Springfield, VA 22161 

## This report wasprintedspecificallyforyourorder from nearly3million titlesavailablein ourcollection. Foreconomyandefficiency, NTISdoesnotmaintainstockofits vastcollection oftechnical reports. Rather, mostdocumentsare custom reproducedforeachorder. Documentsthatare notin electronicformatare reproducedfrom masterarchivalcopies andarethebestpossible reproductionsavailable. Ifyou havequestionsconcerningthis documentoranyorder you haveplacedwith NTIS, pleasecallourCustomerService Departmentat

### 1-888-584-8332or

### (703)605-6050. 

## About NTIS NTIScollectsscientific,technical, engineering,and related businessinformation-thenorganizes, maintains,and disseminatesthatinformation in avarietyofformals- including electronicdownload,onlineaccess, DVD, CD-ROM, magnetic tape, diskette, multimedia, microficheand paper. The NTIScollection ofnearly

## 3 milliontitles includes reports describing researchconductedorsponsored byfederal agenciesandtheircontractors;statisticalandbusiness information; U.S.militarypublications;multimediatraining products;computersoftwareandelectronicdatabases developedbyfederalagencies;andtechnical reportsprepared byresearchorganizationsworldwide. Formore informationaboutNTIS,visitourWebsite at

### http://www.ntis.gov. 

# • NTIS Ensuring Permanent, Easy Access to U.S. Government Information Assets¢OFCo



## ~~**~**

# ...,,

**~** 

# 1Af ;

**\,~,1'** 

# ..

..,...

# "' US,DEPARTMENTOFCOMMERCE TechnologyAdminislrofion NofionolTechnicollnformofionService Springfield,VA 22161 (703)605·6000 

## lllllllllllllllllllllllllllllllllllllllllllllllllllllllllli: llllllllllllllllllll\1111 BIN: M3121 1216-27-1217 INVOICE: 1661132 SHIPTO: 1*979351 PAYMENT: CSH*V