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A

PHARMACEUTICAL SALTS: Table 1. Acids: Alphabetical Oi.der

PROPERTIES. SELECTION, AND USE
Table I (cont.)

335

pK,?

:lass Acid

lMr

pKa~

pKa2

I
1 l~cetic acid

AD1 up to [lngkg
11,s.

;RAS Status

Class Acid

M,

pK,z

pK,,

AD1 GRAS up to Status [mg/k€l

3
1
2

Acetic acid. 2.2-dichloroAdipic acid Alginic acid L-Ascorbic acid L-Aspartic acid Benzenesulfo~licacid Benxoic acid Benzoic acid, 4-acelamido(+)-Camphoric acid (+)-Camphor- 10-sulfonic acid Capric acid (rlecanolc acid) Caproic acid (hexanoic acid) Caprylic acid (octanoic acid) Carbonic acid Cinnamic acid Citric acid Cycla~nic acid Decanoic acid (see cupric acid) Dodecylsulfuric acid Ethane-1.2-disullonic acid Erhanesulfon~cacid Erhanesulfonic acid, 2.hydroxyFornlic acid Fumaric acid Galactaric acid Gentisic acid u-Glucohrptonic acid D-Gluconic acid u-Gluctlronic acid Glutamic acid Glutaric acid Glurnric acid, 2-0x0Glycerophosphoric acid

60.05 128.95 146.14 240 000 176.13 133.11 158.18 122.12 179.18 200.24 232.29 172.27 6 6 144.22 44.01 148.16 192.13 179.24 266.40 190.20 110.13 126.13 46.02 116.08 210.14 154.12 226.18 196.16 194.1J 147.13 132.12 146.10 172.08

4.756 1.35 4.44
2.4

A

3
1

Hydrobromic acid Hydrochloric acid lsobutyric acid DL-Lacric acid Lactobionic acid Lauric acid Maleic acid (-)-L-Malic acid Malonic acid DL-Mandelicacid Methanesulfonic acid Mucic acid (see galacraric acid)

80.92 36.46 88.1 1 90.08 358.30 200.32 116.08 134.09 104.06 152.15 96.10

<-6 -6 4.86 3.86 3.2
4.9

A

2 1 2

1 1

4.17 1.88 0.7 4.19

1
1 1

2
2

1.92 3.459 2.826 3.372 -1.2

3 2 3
1

4.3 4.7 16 2.1 7
4.9 4.8 4.9 1 6.46 4.404 3.128

2 3 2
2

3

2
1

2
2
2

Naphthaicne-1,s-disulfonic acid 1332.26 Naphthalene-2-sulforlic acid 208.24
2-Naphthoic acid. I-hydroxyNicotinic acid Nitric Acid Octanoic acid (see capr?;lic acid) Oleic acid Orotic acid Oxalic acid Palmitic acid Pamoic acid (emhonic acid) Phosphoric acid Propionic acid (-)-L-Pyroglutamic acid Salicylic acid 188.17 123.11 63.02 282.45 156.10 90.04 256.42 388.38

-3.37
0.17

2.7
4.8: -1.32
cn. 4

3
1

2
2

-2.01
-0.09

3
2

2 2 2
3
1

-2.1 2.05
1.66

2 2 1 2
1

5.85
1.271 4.9 2.51 1.96 4.87 3.32 2.97 3.25 4.59 4.9 4.207 -3 3.02

3.75 3.03 3.08 2.93

1 2
1 1

2 2
3

I:
129.1 1 138.12 153.14 202.25 284.49 118.09 98.08 150.09 59.09 172.21 184.27

1
1
1

3.3 3.76 3.18 2.19
4,34

3 ISalicylic acid. 4-amino1 Sebacic acid
I
1

SlFariCacid Succinic acid Su1ful.i~ acid (+)-L-Tartaric acid Thiocyanic acid p-Toluenesulfonic acid Undecylenic acid (undec- 10-enoic acid)

,

2 1

2.7
1.47 3.28
3.55

1
1

76.05 Glycolic acid Hexanoic ;~cld (see ciiproic acid) 179.17 1 Hippuric acid

1

1 2

-1.33
-1.34
4.9

3

- N - N N N - m N ~ N ~ N m - ~ - - - ~ m - ~ ~ N ~ ~ rcl U . Z .? N C E: 3 4 4 4 z g q & 2 w . -rW n m N a m 5C q bi . m a m a g~ n 8 ~ 9 ~~ ~ u d m m ~ a ~ N m ~ ~ A u 0 Pi 4 5 Y G E D 3 $ n r .2 2 + + + m vl Q 2 b + I Q 9a h ='5 c c 4 + L Q c 4 0 a 2 U 5 m . 2 I . m y .- 2 N 4 4 4 4 4 io r' m 4 4 4 4 4 4 4 4 a a ~ y - w N \D e \ d n I A m P I ' q ? - v .m .vl 5 7 + . l ? m oo lm" ~? m o m o *? w ?m F E m r ' Q m N 1 9 ~ F ~ y ~ - h h " . 1 I. - g v I ~ I -I 4 ~ . . b b 2 2 2 -Q >-. r r r r r q ~ ~ ~ ~ 0 ~ ~ ~C< m ~ m p -z > $ 3 T s- o a ~ ~ m m n - m s ~ ~ ~ 9 9 8 ~ 9 ~ 1a.m ~ a i G % & 6 & i i & m . a G N * . ..I I I o ~ N a a m o + . ~ ~ N ~ C ~ ~ 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 . z z ~ q g .

11 90.33 Glutamic acid Cinnamic acid (+)-L-Tartaric acid DL-h.08 96.09 60.02 59.92 4.05 80.86 1. AND USE Table 3 (cont. 2.01 46.1.34 3.05 3.338 PHARMACEUTICAL SALTS: Table 3.85 1.landelic acid Salicylic acid.46 3.02 74.27 1 3.10 146.86 -1.32 4. 4-aminoGer~tisic acid Orotic acid Beozenesulfonic acid Glycerophosphoric acid p-Toluenesulfonic acid Capric acid (decanoic acid) L-Ascorbic acid Hippuric acid Benzoic acid.Acids: Sorted by hzcreusiiig Molec~~lulWeight I PROPERTIES.08 76.10-enoic acid) 2-Naphthoic acid.09 128.66 1 1 2 1 1 2 1 1 3 1 2 2 2 Nicotinic acid 23.35 3.06 110.459 3 1 2 2 1 2 2 2 146.95 129.) 339 I I Decanoic acid (see cap)-icuci0) Hexanoic acid (see cup!-oic acid) Mucic acid (see galucruric ucid) Octanoic acid (see cupplic acid) 1 1 3 Class Acid 1 3 1 36.32 4.1 1 Ethmesulfonic arid.09 -6 6.2 1.92 88.12 3 2 1 1 1.75 -1.28 1 2 1 1 1 3 2 1 3 2 2 1 < -6 4.13 116. 4-acetamidoCyclamic acid Undecylenic acid (undec.03 1. SELECTION.756 -1.8 4.207 4.96 -3 2.46 44.1 1 132. 2-l1yd1~0xy-(126.00 98.08 116. I-hydroxyEthane-1.826 3 2 3 2 2 1 2 1 1 2 2 1 1 2.13 Acetic acid.2-dichloro(-)-L-Pyroglutamic acid Glutaric acid L-Aspartic acid 134.87 3.2-disulfonic acid Citric acid D-Glucuronic acid U-Gluconic acid (+I-Camphoric acid Lauric acid Sebacic acid Naphthalene-2-sulfc~nicacid Galaclaric acid D-Glucoheptonic acid (+)-Camphol--10-sulfonic acid Palmitic acid Dodecylsulful~icacid Oleic acid Stearic acid Naphthalene.04 90.05 63.08 104.10 98.16 118.s-disulfouic acid Lactobionic acid Pamoic acid (ernbonic acid) Alginic acid 7 Status Hydrochloric acid 3 3 2 2 2 Gal-bonic acid Forniic acid Thiocyanic acid Acetic acid Nitric Acid Propionic acid Glycolic acid Hydrobromic acid Isobutyric acid Oxalic acid DL-Lactic acid Metha~iesulfoilic acid Phosphoric acid Sulfuric acid Malonic acid Ethanesulfonic acid Fumaric acid Maleic acid Caprolc acid (hexanoic acid) Succinic acid Benzoic acid 1 1 4.08 116. .44 - 2 .14 4.

38 74.9 .34 A8.05 1.27 c-6 3. AD1 GRA.24 144.12 153.5 A 2.32 -1.s.716 4.92 152.1 2.08 129.95 179.2-dichloroBeuzoic acid.09 + A A -1. I-hydroxyNicotinic acid Olzic acid Orotic acid Oxalic acid Pamoic acid (embonic acid) Propionic acid (-)-L-Pyroglutamic acid A A 13.87 3.18 122.rc a c i d ) Hexanoic acid (see c(ip!-oicacid) blucic acid (see galactaric arid) 10ctanoic acid (see caprvlic acid) Class 1 Acetic acid Adipic acid L-Ascorbic acid L-Aspartic acid Capric acid (decanoic acid) Carbonic acid Citric acid Furnaric acid Galactaric acid D-Glucoheptonicacid D-Gluconic acid D-Glucuronic acid Glutamic acid Glutnric acid Glycerophosphoric acid Glycolic acid Hippuric acid Hydrochloric acid DL-Lacticacid Lauric acid Maleic acid (-)-L-Malic acid Paltnitic acid Phosphatic acid Sebacic acid Straric acid Succinic acid Sulfuric acid (+)-L-Tartaric acid Thiocyanic acid Class 2 Alginic acid Benzenesulfonic acid Benzoic acid 240 000 2 2.04 388.15 156. + + Salicylic acid.95 A 4.35 4.24 188.11 172.17 4.13 126.75 1 46.1 1 358.826 -1.7 4.02 80.40 190.266 A 3.37 0. 2.4 0. 2-0x0Isobutyric acid Lactobionic acid MaIonic acid Methanesulfonic acid 200. 1 A A A 5.06 96.12 146.3 2. 4-acetamido(+)-Camphor-10-sulfonic acid Caproic acid (hexanoic acid) Cinna~nic acid Formic acid Hydrobromic acid DL-Mandelic acid Nitric Acid Salicylic acid A A A A A A A A 128.340 PHARMACEUTICAL SALTS: Table 4.18 232.1 A + A I I 1 I p-Toluenesulfonic acid Class 3 Acetic acid. SELECTION. + 5.13 154.10 90.7 158.97 3.26 Naphthalene-2-sulfonic acid 2-Naphtlloic acid.12 4. 4-aminoUndecylenic acid (undec-10-enoic acid) 3.07 A B A A A n.22 179.10 88.02 138.17 2.83 A A A . 2-hydroxyGentisic acid Glutaric acid.s.17 123.11 282.5-disulfonic acid 332.) Acid Mr PK~I PKS pKa.20 110.14 184.01 -0.85 1.404 3.7 4.2 -3.10 208.16 148.85 ca.! up to Status Imglkgl n.19 A (+)-Camphoric acid Caprylic acid (octanoic acid) Cyclamic acid Dodecylsulfuric acid Ethane-1.9 1 A 5.5 A A -2.2-disulfonic acid Ethanesulfonic acid Ethanesulfonic acid.29 1 16.93 2. Acids: Sorted by Class PROPERTIES.30 104.16 1.372 -1.s.64 A A A I Naphthalene-l.5 A A A A4.271 2.8 4. AND USE 34 1 I pK.25 A A A 13.15 63.3 AD1 GRAS up to Status [mglkgl Table 4 (cont. Acid Mr pK3 I pKaz Decanoic acid (see capr.32 2.24 266.82 A A I0 A A n.696 A A -2.5 B A A 4.66 2.-2.2 2.86 3.51 4.21 4.

f $ Z * 3 ~ O \ ' mr* o ~ q rg ! ~ .P .o & $ . = c ~ ~ ~d d ~ .~ .a - ' m m - ~ . ~ ~ 9 ..ri ri m m m m m m m m m m m m m m m m m m m m m m m m m m m m m m m m m m Pi m m m m m m m m - 4 m m m m m m m m m m m m m m m m m m m m m m m m I 2 9 P o m l n m rn r?r ?v-oIqq 0 c ffi C Z 2 3 . .m N L ? C\ o O 2 .

m .C O m 0. - B m m m m m m m m m m m m m m m m m m m m m m m m m m m .m m m m m m m m m m m m m m m m m m m rn m m m m m m F a - 7 '0 m m m m t'?N - m G ' cn -f m m 8 .