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Citric Acid

A carboxylic acid, C6H8O7, 192.123 g/mol. Boiling point Decomposes, melting point 153 °C, as published.

verified record, Organic — carboxylic acid, 8 measured properties

Identifiers

Molecular formula
C₆H₈O₇
Molecular weight
192.123 g/mol
Exact mass
192.027003 g/mol
IUPAC name
2-hydroxypropane-1,2,3-tricarboxylic acid
SMILES
O=C(O)CC(O)(CC(=O)O)C(=O)O
InChI
InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
InChIKey
KRKNYBCHXYNGOX-UHFFFAOYSA-N

Measured properties

Published measurements, each with its source. Two readings of one property are both shown, in the units each used.

Boiling Point
Decomposes (NTP, 1992)measured · CAMEO Chemicals
Decomposesmeasured · Hazardous Substances Data Bank (HSDB)
Melting Point
307 °F (anhydrous) (NTP, 1992)measured · CAMEO Chemicals
153 °Cmeasured · DrugBank
Density
1.54 at 68 °F (USCG, 1999) - Denser than water; will sinkmeasured · CAMEO Chemicals
1.665 g/cu cm at 20 °Cmeasured · Hazardous Substances Data Bank (HSDB)
Solubility
greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)measured · CAMEO Chemicals
592000 mg/L (at 20 °C)measured · DrugBank
LogP
-1.64measured · DrugBank
log Kow = -1.64measured · Hazardous Substances Data Bank (HSDB)
Flash Point
100 °Cmeasured · ILO-WHO International Chemical Safety Cards (ICSCs)
Viscosity
2.549 cP 30% aqueous solution at 20 °Cmeasured · Haynes, W.M. (ed.) CRC Handbook of Chemistry and Physics. 91st ed. Boca Raton, FL: CRC Press Inc., 2010-2011, p. 8-55
Refractive Index
INDEX OF REFRACTION: 1.493, 1.498, 1.509 @ 20 °C /CITRIC ACID HYDRATE/measured · Furia, T.E. (ed.). CRC Handbook of Food Additives. 2nd ed. Cleveland: The Chemical Rubber Co., 1972., p. 244
Index of refraction (30% solution): 1.3744 at 20 °C/Dmeasured · Haynes, W.M. (ed.) CRC Handbook of Chemistry and Physics. 91st ed. Boca Raton, FL: CRC Press Inc., 2010-2011, p. 8-55

Calculated properties

Derived from the structure, not from a sample; kept apart from the measurements above.

Molecular weight
192.12 g/molcalculated · reference compound database
Average mass of one molecule, from reference compound database.
Exact mass
192.02700259 Dacalculated · reference compound database
Mass of the most common isotopic form.
XLogP3
-1.7calculated · reference compound database
Estimated oil/water partition, computed by reference compound database.
Polar surface area
132 Ųcalculated · reference compound database
Polar surface area as computed by reference compound database.
Complexity
227calculated · reference compound database
A rough measure of how intricate the structure is.
H-bond donors
4calculated · reference compound database
H-bond acceptors
7calculated · reference compound database
logP
-1.2485calculated · chemistry engine
Estimated preference for oil over water. Higher means more oil-like.
Topological polar surface area
132.13 Ųcalculated · chemistry engine
Surface area from polar atoms; relates to how easily a molecule crosses membranes.
H-bond donors
4calculated · chemistry engine
Atoms that can donate a hydrogen bond.
H-bond acceptors
4calculated · chemistry engine
Atoms that can accept a hydrogen bond.
Rotatable bonds
5calculated · chemistry engine
Single bonds the molecule can freely twist around.
Molar refractivity
37.0912 cm³/molcalculated · chemistry engine
Relates to the molecule's polarisability.
Fraction sp³ carbons
0.5calculated · chemistry engine
Share of carbon atoms with tetrahedral bonding.
QED drug-likeness
0.4274calculated · chemistry engine
Quantitative estimate of drug-likeness (0–1).

What it is made of

Elements

Percentages are of the molecular weight above, worked out the same way the molar mass calculator does it.

Structure

Heavy atoms, hydrogen excluded
13
Total atoms, hydrogen included
21
Rings
0
Aromatic rings
0
Stereocentres
0
Formal charge
0

Functional groups

  • Carboxylic acid

    A carbon double-bonded to oxygen and bonded to an –OH group; acidic.

  • Alcohol

    An –OH group on a saturated carbon.

Matched by structural pattern, not by a measurement.

The molecule in three dimensions

Rotate and inspect the atoms. Loaded only when you ask, so the page stays light.

The drawing above is a diagram of what is bonded to what. A molecule is not flat, and the model here is one low-energy shape generated from the connectivity — useful for seeing which groups can reach each other, and not a measured structure. A real sample is a population of conformations, interconverting.

Reactions it appears in

No documented reaction with a written procedure and a source involves Citric Acid yet.

Other names for it

The systematic name on this record is 2-hydroxypropane-1,2,3-tricarboxylic acid.

The sources also call it 2-hydroxypropane-1,2,3-tricarboxylic acid, Citric acid, anhydrous, Aciletten, Anhydrous citric acid, Citro, Citretten, Citric acid anhydrous, Chemfill, Hydrocerol A, 1,2,3-Propanetricarboxylic acid, 2-hydroxy-, 2-hydroxy-1,2,3-propanetricarboxylic acid.

Structurally related

Nothing structurally close to Citric Acid has a page here yet.

Seen alongside it in reaction records

Molecules that appear in the same recorded reactions as Citric Acid. This says nothing about structure: most of them are the bases, solvents, ligands and catalysts the chemistry needed, and they are here because somebody put them in the same flask.

Where these values came from

compound record.

What this page does not claim

Identifiers are copied from the source record, measured values are reported as published, and calculated values are marked as calculated. Nothing here is a hazard, purity or handling assessment — how the library is checked.