`
`)ME EDITION
`
`THE
`
`MERCK INDEX
`
`
`
`AN ENCYCLOPEDIA OF
`
`
`
`CHEMICALS, DRUGS, AND BIOLOGICALS
`
`THIRTEENTH EDITION
`
`
`
`Editorial Staff
`
`�aryadele J. O'Neil,
`
`
`Senior Editor
`
`Ann Smith,
`
`
`
`Senior Associate Editor
`
`
`Patricia E. Heckelman,
`
`Associate Editor
`
`John R. Obenchain Jr., Editorial Assistant
`
`
`Jo Ann R. Gallipeau,
`
`Technical Assistant
`Mary Ann D' Arecca,
`
`
`Administrative Associate
`
`Susan Budavari,
`
`Editor Emeritus
`
`Published by
`
`
`Merck Research Laboratories
`
`Division of
`
`MERCK & CO., INC.
`
`
`Whitehouse Station, NJ
`
`BMS 2012
`MYLAN v. BMS
`IPR2018-00892
`
`1
`
`
`
`MERCK & CO., INC.
`
`
`Whitehouse Station, NJ
`USA
`
`!st Edition-1889
`
`2nd Edition-1896
`
`3rd Edition-1907
`
`4th Edition-1930
`
`5th Edition-1940
`
`6th Edition-1952
`
`7th Edition-1960
`
`8th Edition-1968
`
`9th Edition-1976
`
`10th Edition-1983
`
`11th Edition-1989
`
`12th Edition-1996
`
`Library of Congress Catalog
`
`Card Number 89-60001
`ISBN Number 0911910-13-1
`
`Copyright© 2001 by MERCK & CO., INC.
`
`
`
`
`
`
`All rights reserved. Copyright under the Universal Copyright Convention
`
`
`and the International Copyright Convention.
`
`
`
`
`Copyright reserved under the Pan-American Copyright Convention.
`
`
`
`Printed in the USA
`
`2
`
`
`
`Sucralose
`
`8965
`
`0-N=N-C
`
`Dec 160-186heating to 90°. di5 1.587. °. Chars and emits char
`
`
`
`[a]g' not less than +65.9° (c = 26);
`odor of caramel.
`acteristic
`usual value [a]f;S +66.47 to +66.49°. One gram dissolves
`in
`
`
`
`
`
`0.5 ml water; in slightly more than 0.2 ml boiling water, in 170
`
`
`
`ml alcohol; in about 100 ml methanol. Moderately sol in glyc
`
`erol, pyridine. pKa 12.62. d� of water solns (g/100 g): 2%
`
`
`
`1.0060;,6% 1.0219; 10% 1.0381; 20% 1.0810; 30% l.1270·
`
`40% 1.1764; 50% 1.2296; 60% 1.2865; 70% 1.3471;
`76%
`
`
`
`
`nt0 of 10% soln 1.34783. Sucrose does not reduce
`1.3854.
`Fehl
`Brown leaves with green metalli
`
`
`
`ing's soln, form an osazone, or show mutarotation. It is hydro.
`
`
`
`lyzed to glucose and fructose by di! acids and by invertase, a
`water or lye. Slightly sol in hot gl:
`
`White amorphous powder. Sol in di! HCL and NaOH solns.
`
`
`
`
`roform; moderately sol ether, acetc
`
`
`
`
`yeast enzyme. Upon hydrolysis the optical rotation falls and is
`
`
`Practically insol in water, ethanol, CHCJ3• pKa = 0.43 to 1.19.
`
`
`
`
`
`negative when the hydrolysis is complete. The mixture of glu
`
`atile oils, hot glycerol.
`Sol in alco
`
`
`
`
`
`Dissolution of aluminum occurs at pH <3; of sucrose sulfate at
`
`
`
`
`cose and fructose is known as "invert sugar." Sucrose is fer
`
`usE: Dye. Biological stain.
`pH >4.
`
`
`
`but resists bacterial decompn when in high concen
`mentable,
`THERAP CAT: Antiulcerative.
`8970. Sudan Black B. [ 419
`trations.
`
`methyl-6-[[ 4-(phenylazo)-1-naphti
`
`
`8965. Sucralose. [56038-13-2] l,6-Dichloro-l,6-dideoxy
`
`
`
`Caution: Potential symptoms of overexposure are irritation
`
`C.I. Solvent Black 3; C.I. 26150;
`/3-D-fructofuranosyl-4-chloro-4-deoxy-a-D-galactopyranoside;
`
`
`of eyes, skin, upper respiratory system; cough. See NIOSH
`C29H24N6; mol wt 456.54.
`C 76.
`
`
`
`4, 1 ',6' -trichloro-4, l ',6' -trideoxy-galacto-sucrose; l ',4,6' -trichlo
`
`Hazards (DHHS/NIOSH 97-140,
`Pocket Guide to Chemical
`
`Lipid dye comprised of two maj,
`C rogalactosucrose; TGS. C12H19CJ308; mo! wt 397.64.
`
`
`1997) p 288.
`
`
`SBB-11 and at least 12 secondary cc
`
`
`
`
`36.25%, H 4.82%, Cl 26.75%, 0 32.19%. Chlorinated sucrose
`
`
`
`USE: Sweetening agent and food. Starting material in the
`
`by the chemical name and CAS r,
`
`
`
`derivative with enhanced sweetness. Prepn: P. H. Fairclough
`
`
`
`
`ferrnentative production of ethanol, butanol, glycerol, citric and
`duced: L. Lison,
`
`
`Res. 40, 285 (1975). Prepn of crystalline an
`
`Comptes. Rend.
`
`
`
`
`Jevulinic acids. Used in pharmaceuticals as a flavor, as a pre
`et al., Carbohyd.
`
`TLC purification and histochemist
`
`
`
`
`hydrous and pentahydrate: M. R. Jenner, D. Waite, EP 30804
`
`
`
`
`servative, as an antioxidant (in the form of invert sugar}, as a
`
`16, 68 (1968); and solve
`
`
`
`(1981 to Tate & Lyle; Talres Dev.); eidem, US 4343934 (1982
`tochemie
`
`
`
`
`demulcent, as substitute for glycerol, as granulation agent and
`
`Suppl. 24,
`
`
`
`to Talres Dev.). Use as non-nutritive sweetener: BE 850180;
`et al., Acta Histochem
`
`
`
`
`
`excipient for tablets, as coating for tablets. In the plastics and
`
`dation: U. Pftiller
`
`L. Hough et al., US 4435440 (1977, 1984 both to Tate & Lyle).
`et aL, Histochen
`
`
`
`cellulose industry, in rigid polyurethane foams, manuf of ink
`
`
`ing technique: D. A. Nelson, F.
`
`
`
`
`In vitro activity vs cariogenic bacteria: J. Verran, D. B. Drucker,
`
`and of transparent soaps.
`
`
`Staining" in Hematology, W. J. Wi
`
`
`Arch. Oral Biol. 27, 693 (1982). Structure-sweetness relation
`
`Hill Publishing Co., New York, l'
`C28H38019; mol
`ship: M. Mathlouthi
`Res. 152, 47 (1986).
`
`
`8967. Sucrose Octaacetate. [126-14-7]
`et al., Carbohyd.
`Re
`
`
`
`lipid stain: H. N. Subramaniam, I
`
`
`
`wt 678.59. C 49.56%, H 5.64%, 0 44.80%. Prepn from su
`
`
`view: L. Hough, R. Khan, Trends Biochem. Sci. 3,61-63 (1978).
`Methods 21, 9 (1990).
`
`et al., J. Am. Chem. Soc. 62, 3260 (1940). Syn
`
`crose: Linstesld
`Biophys.
`
`
`
`thesis: Lemieux, Huber, ibid. 78, 4117 (1956).
`mp 89°;
`
`
`
`
`Hygroscopic, intensely bitter needles from alcohol,
`dee above 285°; bp1 260°. [a]f;S.4 +58.5° (c = 2.56 in abs al·
`0.7
`
`
`
`coho!). n0 1.4660. Sol in 1100 parts water, 1.1 parts acetal,
`0.6
`
`
`
`part glacial acetic acid, 0.3 part acetone, 11 parts alcohol,
`
`
`part benzene, 22 parts carbon tetrachloride, about 0.5 part me
`
`
`
`thyl acetate, 7 parts paraldehyde, about 0.5 part toluene.
`
`
`
`
`USE: Adhesive; impregnating and insulating papers; in lac
`
`
`quers and plastics; as a denaturant for alcohol.
`
`
`
`8968. Sucrose Polyester. Olestra; SPE. Non-absorbable
`
`
`
`Anhydrous crystalSyrup, [a]0 +68.2° (c = 1.1 in ethanol).
`
`
`
`
`
`lipid; substitute for fat in foods to reduce cholesterol level. Mix
`
`
`mp 130°. Inline form: orthorhombic, needlelike crystals,
`
`
`
`
`
`ture of hexa-, hepta-and octa-fatty acid esters of sucrose. Anal
`Sudan Black B 1
`
`Khan). tensely sweet taste. LD50 in mice: >16 g/kg (Hough,
`
`
`
`
`
`ysis by gel permeation chromatography: C. G. Birch, F. E.
`
`Pentahydrate. mp 36.5°.
`
`
`Crowe, J. Am. Oil Chem. Soc. 53, 581 (1976). Effect on ab
`
`
`Basic compound completely decc
`
`
`8966. Sucrose. [57-50-1] /3-D-Fructofuranosyl-a-D-glu
`
`
`
`sorption of dietary cholesterol in rats: F. H. Mattson
`Sudan Black B I. SBB-1; SSB-l
`et al., J.
`
`
`copyranoside; a-D-glucopyranosyl-/3-D-fructofuranoside; sugar;
`
`Nutr. 106, 747 (1976); L. Aust et al., Ann. Nutr. Metab. 25, 255
`4[( 4-phenylazo-1-naphthalenyl)-azo
`
`saccharose; cane sugar; beet sugar. C12H220,,; mo! wt 342.30.
`
`( 1981 ). Effects as a dietary agent for lowering plasma choles·
`
`compound, mp 180-186
`
`° (dee). S1
`
`
`C 42.11%, H 6.48%, 0 51.41%. Obtained from sugar cane
`terol in man: R. W. Falla!
`et al., Am. J. Clin. Nutr. 29, 1024
`
`torr Without decompositon.
`
`ojjicinarum L., Gramineae) and sugar beet (Beta
`Effects on
`(1976);
`C. J. Glueck et al., ibid. 32, 1636 (1979).
`(Saccharum
`
`USE: Biological stain for lipids.
`
`
`L., Chenopodiaceae). Sugar cane contains from 15-
`S. M. Grundy,
`
`
`cholesterol metabolism in man: J. R. Crouse,
`valgaris
`
`8971. Suet, Prepared. Mutto
`
`
`
`20% and sugar beet from 10-17% sucrose. Structure: Avery et
`
`Clin. Exp. 28, 994 (1979); R. J. Jandacek
`Metab.,
`et al., Am. J.
`
`abdomen of sheep purified by melti
`
`
`al., J. Chem. Soc. 1927, 2308; Beevers, Cochrane,
`
`
`Clin. Nutr. 33, 251 (1980). Caloric dilution study in obese pa
`
`Proc. Roy.
`White,
`
`
`Soc. 190A, 257 (1947). Synthesis: Pictet, Vogel,
`
`solid fat with slight odor 2
`
`tients: C. J. Glueck et al., ibid. 35, 1352 ( 1982).
`Helv. Chim.
`;ancid after Jong exposure
`
`
`
`Acta 11, 436 (1928); Lemieux, Huber, J. Am Chem. Soc. 78,
`to air. n
`
`USE: As supplement in dietary foods.
`ai3pon no. 192-195.
`
`Iodine no. 33-
`
`
`4117 (1956). Ref. with extensive bibliography: Bates,
`Polarim
`
`cohoJ; one gram dissolves in 45 n
`enyl]·
`
`8969. Sudan m. [85-86-9] 1-[[4-(Phenylazo)ph
`
`
`
`etry, Saccharimetry, and the Sugars, National Bureau of Stan
`rnJ ether.
`ol; te·
`
`
`azo ]-2-naphthalenol; 1-(p-phenylazophenylazo )-2-naphth
`
`C440, Washington, 1942; W. Pigman,
`dards Circular
`The Car
`D & C Red No. 17; C.I. Solvent Red
`USE: Preparing ointments.
`
`
`(Academic Press, New York, 1957) pp 501-506.
`trazobenzene-/3-naphthol;
`bohydrates
`Re
`23; C.I. 26100; Sudan Red BK; Tony Red. C22H16N40; mol wt
`views: M. R. Jenner,
`2, 91-143 (1980);
`1_ 8972 .. Sufentanil.
`Dev. Food Carbohyd.
`[56030-54-'
`0 4.54%. Weakly
`R. Khan, Pure Appl. Chem. 56, 833 (1984).
`[2-(2-thienyl
`
`
`352.39. C 74.98%, H 4.58%, N 15.90%,
`[ 4
`)ethyl]-4-piperidinyl]
`as a fat stain in J 896.
`-(�ethoxymethyl)-l-[2-(2-thic
`
`
`acidic azo dye; originally introduced
`Colour Index vol. 4
`r;;op1onanilide;
`
`Prepn: R. Nietzki, Ber. 13, 1838 (1880);
`sufentanyl;
`R-3073
`J> 6.56. C 68.36%,
`
`(3rd ed., 1971) p 4227. Description: H. J. Conn• s Biological
`H 7,82%, N 7
`
`
`R. D. Lillie, Ed. (Williams & Wilkins, Baltimore, 9th
`y°tent deriv of fentanyl;
`
`q. v. Prepn:
`Stains,
`
`ed., 1977) pp 168-169, 576. HPLC determn in cosmetics: J.
`J an Daele, DE 2610228;
`
`eidem, l
`LC/el�C
`1�;ssen); G. H. P. Van Daele et al
`W. Wegener
`24, 865 (1987);
`et al., Chromatographia
`H.-Y. f:,1�
`l 0976). In vitro binding
`
`
`
`trospray-MS determn as environmental contaminant:
`prope
`J. E
`
`R. D. Voyksner, Anal. Chem. 65,451 (1993). Use as biologic
`
`26o · Leysen, W. Gommeren,
`Arch
`Meth. 5, 135 (1982); p..
`287 (1982);
`
`stain: W. Frisch-Niggemeyer,
`J.E. Leyson et al.,
`J. Virol.
`098
`StrUcture
`13 3). Analgesic
`
`
`
`
`
`Monoclinic sphenoidal crystals, cryst masses, blocks, or pow
`Kishida
`Release 13, 83 (1990).
`activity
`and safet)
`et al., J. Controlled
`N�Ver et al., Arzneimittel-Forsc
`
`
`
`
`der. Sweet taste. Stable in air. Finely. divided sugar is hygro
`
`
`effects on dye adsorption: H. L. Needles
`et al., Colourage An/lU·
`h.
`iemegeers et al., ibid.
`
`
`
`scopic and absorbs up to 1 % moisture which is given up on
`1995, 115.
`1551. GC d
`
`Page 1582
`
`
`
`Consult the Name Index before using this section.
`
`3
`
`3
`
`