BROWSE BY STRUCTURE

Hydroxy Carboxylic Acids

Structures, Properties, Uses, Comparisons & Suppliers

What Connects This Family?

These carboxylic acids contain a hydroxyl group in addition to the hydroxyl within each COOH group. The extra group can affect hydrogen bonding, polarity, acid–base behavior and reaction options; it does not guarantee a universal solubility or performance advantage.

Lactic and mandelic have an alpha hydroxyl; salicylic has a phenolic hydroxyl on an aromatic ring. Malic and tartaric are also diacids, while citric has three carboxyl groups. Stereochemistry matters when the structure contains stereocenters.

Sources: OpenStax · Structure and properties of carboxylic acids (opens new tab) · OpenStax · Substituent effects on acidity (opens new tab)

Membership and structural distinctions are grounded in the linked identity records in the comparison below. The categories overlap intentionally.

Compare the Current Examples

Identity, carboxyl count, pKa context and structural distinctions
Acid / formulaCarbons / COOHProfile formpKa referenceStructural distinction / specification
3-Hydroxybenzoic AcidC₇H₆O₃ · CAS 99-06-97 carbons
1 COOH
Neutral free acid; water and derivatives specified separatelySee compound referenceNo number repeated here.COOH defines ring position 1 and OH occupies position 3. There is one carboxyl group, not two; the phenolic proton is a separate acid-base site. The neutral structure is achiral.TCI reports HPLC area% and neutralization titration separately; Sigma’s 99% method is unstated; Thermo’s 99% headline has a minimum 98.5% HPLC specification. None is a verified pharma or cosmetic ingredient grade. Positional identity is independent of total acid assay.Identity source (opens new tab) · Technical reference
4-Hydroxybenzoic AcidC₇H₆O₃ · CAS 99-96-77 carbons
1 COOH
Neutral free acid; water and derivatives specified separatelySee compound referenceNo number repeated here.OH and COOH occupy opposite ring positions, 1 and 4. The phenolic hydroxyl does not make this a dicarboxylic acid, and the molecule has no stereocenter.The Wako 100 mg qNMR/HPLC standard is not equivalent to TCI or Sigma bulk reagents. Food analysis is not food-ingredient grade. Keep positional identity, assay method and ester identity distinct.Identity source (opens new tab) · Technical reference
Citric AcidC₆H₈O₇ · CAS 77-92-96 carbons
3 COOH
Solid · anhydrous identity3.128 / 4.761 / 6.396 (25 °C, water, zero ionic strength)Reference & conditions (opens new tab)Three carboxyl groups and one additional hydroxyl group.Specify anhydrous or monohydrate, assay basis, and the required application specification.Identity source (opens new tab) · Technical reference
Gallic AcidC₇H₆O₅ · CAS 149-91-77 carbons
1 COOH
Neutral free acid; water and derivatives specified separatelySee compound referenceNo number repeated here.OH groups occupy ring positions 3, 4 and 5. The neutral free acid is achiral; its formula excludes any crystal water. Three phenolic OH groups do not mean three COOH groups.TCI G0011 now labels the free acid and treats moisture as impurity, with up to 10% drying loss and titration after drying. Sigma titration spans 97.5–102.5%. Santa Cruz’s SAMPLE UHPLC result is not a current lot certificate. Fixed monohydrate CAS 5995-86-8 / 188.13 g/mol is excluded from this price table.Identity source (opens new tab) · Technical reference
Gluconic AcidC₆H₁₂O₇ · CAS 526-95-46 carbons
1 COOH
D neutral acid identity; displayed aqueous acid/lactone productsSee compound referenceNo number repeated here.Four CHOH centers carry the stereochemistry of this D identity. The terminal CH₂OH supplies the fifth non-carboxylic hydroxyl. A condensed formula does not encode the four configurations; the IUPAC name and InChI do.All three listings are solutions priced by solution mass. TCI explicitly contains gluconolactone and reports 45–50% w/w titration; Sigma reports 49–53 wt.% without a method; Wako reports 47–53% titration and its SDS confirms weight-% composition. None establishes chemical or optical purity.Identity source (opens new tab) · Technical reference
Glycolic AcidC₂H₄O₃ · CAS 79-14-12 carbons
1 COOH
Free acidSee compound referenceNo number repeated here.The hydroxyl-bearing carbon is CH₂, so it has no stereocenter. The non-carboxylic OH makes this a hydroxy acid; it does not add a second carboxyl group.All three priced entries are solids. Sigma separately lists technical 70 wt.% aqueous glycolic acid; Wako separately lists a 67–73% solution assay without a retrieved explicit mass basis. Neither is treated as 70% chemical purity. A clear-solution test at 50 mg/mL is not saturation solubility.Identity source (opens new tab) · Technical reference
Lactic AcidC₃H₆O₃ · CAS 50-21-53 carbons
1 COOH
Commercial liquids / aqueous solutions3.86 (20 °C, in water)Reference & conditions (opens new tab)A three-carbon alpha-hydroxy acid; L, D and DL forms matter.Specify concentration, chemical assay and method, L/D/DL form, optical specification, water content, and package mass or volume separately.Identity source (opens new tab) · Technical reference
Malic AcidC₄H₆O₅ · CAS 6915-15-74 carbons
2 COOH
Solid · DL identitySee compound referenceNo number repeated here.A hydroxy diacid with one stereocenter; this profile uses DL identity.Specify DL, L, or D form and require stereochemical evidence when relevant.Identity source (opens new tab) · Technical reference
Mandelic AcidC₈H₈O₃ · CAS 90-64-28 carbons
1 COOH
Solid · DL identitySee compound referenceNo number repeated here.A phenyl-bearing alpha-hydroxy acid; this profile uses DL identity.Specify DL, R, or S form and optical-purity requirements separately from chemical assay.Identity source (opens new tab) · Technical reference
Salicylic AcidC₇H₆O₃ · CAS 69-72-77 carbons
1 COOH
Solid2.98 (carboxyl, 20 °C)Reference & conditions (opens new tab)An aromatic acid with a neighboring phenolic hydroxyl.Require the appropriate impurity profile and formulation specification; distinguish titration from HPLC assay.Identity source (opens new tab) · Technical reference
Tartaric AcidC₄H₆O₆ · CAS 87-69-44 carbons
2 COOH
Solid · L-(+) identity3.036 / 4.366 (25 °C, water, zero ionic strength; L-(+) form)Reference & conditions (opens new tab)A hydroxy diacid with two stereocenters; this profile uses L-(+).Require L-(+) identity, stereochemical specification, and separate chemical and optical assay.Identity source (opens new tab) · Technical reference

3-Hydroxybenzoic Acid

Formula
C₇H₆O₃
CAS
99-06-9
Carbon atoms
7
COOH groups
1
Profile form
Neutral free acid; water and derivatives specified separately
pKa and conditions
See compound referenceNo number repeated here.

COOH defines ring position 1 and OH occupies position 3. There is one carboxyl group, not two; the phenolic proton is a separate acid-base site. The neutral structure is achiral.

TCI reports HPLC area% and neutralization titration separately; Sigma’s 99% method is unstated; Thermo’s 99% headline has a minimum 98.5% HPLC specification. None is a verified pharma or cosmetic ingredient grade. Positional identity is independent of total acid assay.

Identity source (opens new tab) · Technical reference

4-Hydroxybenzoic Acid

Formula
C₇H₆O₃
CAS
99-96-7
Carbon atoms
7
COOH groups
1
Profile form
Neutral free acid; water and derivatives specified separately
pKa and conditions
See compound referenceNo number repeated here.

OH and COOH occupy opposite ring positions, 1 and 4. The phenolic hydroxyl does not make this a dicarboxylic acid, and the molecule has no stereocenter.

The Wako 100 mg qNMR/HPLC standard is not equivalent to TCI or Sigma bulk reagents. Food analysis is not food-ingredient grade. Keep positional identity, assay method and ester identity distinct.

Identity source (opens new tab) · Technical reference

Gallic Acid

Formula
C₇H₆O₅
CAS
149-91-7
Carbon atoms
7
COOH groups
1
Profile form
Neutral free acid; water and derivatives specified separately
pKa and conditions
See compound referenceNo number repeated here.

OH groups occupy ring positions 3, 4 and 5. The neutral free acid is achiral; its formula excludes any crystal water. Three phenolic OH groups do not mean three COOH groups.

TCI G0011 now labels the free acid and treats moisture as impurity, with up to 10% drying loss and titration after drying. Sigma titration spans 97.5–102.5%. Santa Cruz’s SAMPLE UHPLC result is not a current lot certificate. Fixed monohydrate CAS 5995-86-8 / 188.13 g/mol is excluded from this price table.

Identity source (opens new tab) · Technical reference

Gluconic Acid

Formula
C₆H₁₂O₇
CAS
526-95-4
Carbon atoms
6
COOH groups
1
Profile form
D neutral acid identity; displayed aqueous acid/lactone products
pKa and conditions
See compound referenceNo number repeated here.

Four CHOH centers carry the stereochemistry of this D identity. The terminal CH₂OH supplies the fifth non-carboxylic hydroxyl. A condensed formula does not encode the four configurations; the IUPAC name and InChI do.

All three listings are solutions priced by solution mass. TCI explicitly contains gluconolactone and reports 45–50% w/w titration; Sigma reports 49–53 wt.% without a method; Wako reports 47–53% titration and its SDS confirms weight-% composition. None establishes chemical or optical purity.

Identity source (opens new tab) · Technical reference

Glycolic Acid

Formula
C₂H₄O₃
CAS
79-14-1
Carbon atoms
2
COOH groups
1
Profile form
Free acid
pKa and conditions
See compound referenceNo number repeated here.

The hydroxyl-bearing carbon is CH₂, so it has no stereocenter. The non-carboxylic OH makes this a hydroxy acid; it does not add a second carboxyl group.

All three priced entries are solids. Sigma separately lists technical 70 wt.% aqueous glycolic acid; Wako separately lists a 67–73% solution assay without a retrieved explicit mass basis. Neither is treated as 70% chemical purity. A clear-solution test at 50 mg/mL is not saturation solubility.

Identity source (opens new tab) · Technical reference

Numerical pKa values are repeated here only for the six independently reviewed profiles, with their reference conditions. Other values remain in the individual technical references. Compare matched identities and conditions; no acidity ratio or solubility ranking is inferred.

Useful Comparisons

Choose another pair →

Buying & Sourcing Hydroxy Carboxylic Acids

Separate chemical assay from optical purity or ee. For lactic solutions, specify concentration, assay basis, water and free-monomer requirements where relevant. For citric, distinguish anhydrous and monohydrate. Match the application specification before using a reagent product in a formulation.