Citramalic acid
Athanor · official
C5H8O5 · 148.11 g/mol
IUPAC name: 2-hydroxy-2-methylbutanedioic acid
Also called citramalate, 2-methylmalic acid
WarningCauses skin irritation · Causes serious eye irritation · May cause respiratory irritationNames and identifiers
- IUPAC name
- 2-hydroxy-2-methylbutanedioic acid
- Synonyms
- citramalate, 2-methylmalic acid, (+-)-Citramalic acid
+ 35 more
RefChem:390712, 2-hydroxy-2-methylbutanedioic acid, 2-Methylmalic acid, 2-Hydroxy-2-methylsuccinic acid, DL-Citramalic acid, 2-Hydroxy-2-methyl-butanedioic acid, 2-Hydroxy-2-methylbutane-1,4-dioic acid, alpha-Hydroxypyrotartaric acid, 2-Deoxy-3-C-methyltetraric acid, (+/-)-Citramalic acid sodium salt, butanedioic acid, 2-hydroxy-2-methyl-, (+/-)-Citramalic acid dipotassium salt, FGC721P65H, NSC-80648, Malic acid, 2-methyl-, UNII-FGC721P65H, methylmalic acid, DL-Citramalate, (b)-Citramalate, EINECS 209-901-5, (b)-Citramalic acid, (1)-2-Hydroxy-2-methylsuccinic acid, (b)-2-Methylmalate, (+-)-2-hydroxy-2-methylsuccinic acid, (RS)-citramalic acid, 2-methyl-(b)-Malate, (R,S)-b-Methylmalate, D -2-Methylmalic acid, (b)-2-Methylmalic acid, (R,S)-beta-Methylmalate, (R,S)-(b)-Citramalate, (r,s)-b-methylmalic acid, 2-methyl-(b)-Malic acid, (L)-(+)-Citramalic acid, SCHEMBL61203
- Molecular formula
- C5H8O5
- Empirical formula
- C5H8O5
- Molecular weight
- 148.11 g/mol
- Exact mass
- 148.03717
- CAS number
- 6236-09-5
- PubChem CID
- 1081
- Canonical SMILES
- CC(CC(=O)O)(C(=O)O)O
- Isomeric SMILES
- CC(CC(=O)O)(C(=O)O)O
- InChI
- InChI=1S/C5H8O5/c1-5(10,4(8)9)2-3(6)7/h10H,2H2,1H3,(H,6,7)(H,8,9)
- InChIKey
- XFTRTWQBIOMVPK-UHFFFAOYSA-N
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Calculated
- Heavy atoms
- 10
- Rings
- 0
- Aromatic rings
- 0
- Fraction sp³ carbons (Fsp3)
- 0.6
- H-bond donors
- 3
- H-bond acceptors
- 3 computed here · PubChem 5
- Rotatable bonds
- 3
- TPSA (Ų)
- 94.8
- Formal charge
- 0
- XLogP3
- -0.9 PubChem
- Complexity
- 163 PubChem
- Stereocenters
- 0 defined, 1 undefinedCIP: C2: undefined
- Double-bond geometry
- None specified
- Point group
- C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)
Elemental analysis
- C40.55%
- H5.44%
- O54.01%
Isotope pattern
Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.
Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.
Predicted
- log P
- -0.7 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- -0.12 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 2.94 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 148.11
- log P ≤ 5 (Crippen): -0.7
- H-bond donors ≤ 5: 3
- H-bond acceptors ≤ 10: 3
Passes all four rules.
¹³C NMR shifts, predicted
Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.
Safety
Warning
Most widely reported: 38 company reports to ECHA. Source [1].
- Harmful or irritant
- H315Causes skin irritation
- H319Causes serious eye irritation
- H335May cause respiratory irritation
Precautionary statements: P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
View all classifications (2)
- [1] European Chemicals Agency (ECHA) · 38 reports · WarningH315, H319, H335
- [1] European Chemicals Agency (ECHA) · 3 reports · WarningH315, H319, H335
Safety data sheets on the supplier’s page: J&H Chemical Co.,ltd, BenchChem, RR Scientific.
Always read the supplier’s safety data sheet before working with it.
Spectra
- 1H NMRHuman Metabolome Database (HMDB) (Varian · 500 MHz · Water) · SpectraBase (Varian CFT-20)
- 13C NMRSpectraBase
- 1H-13C NMRHuman Metabolome Database (HMDB) (Bruker · 400 MHz · Water)
- GC-MSSpectraBase
- MS-MSHuman Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Negative) · Human Metabolome Database (HMDB) (Negative)
- LC-MSMassBank Europe (LTQ Orbitrap Velos Thermo Scientific · LC-ESI-ITFT · NEGATIVE) · MassBank Europe (LTQ XL, Thermo Finnigan · LC-ESI-IT · NEGATIVE) · MassBank Europe (TripleToF 5600; Sciex · LC-ESI-QTOF · NEGATIVE) · MassBank Europe (Agilent 6530 Q-TOF LC/MS · LC-ESI-QTOF · NEGATIVE) · MassBank Europe (Agilent 6530 Q-TOF LC/MS · LC-ESI-QTOF · NEGATIVE) · MassBank Europe (Agilent 6530 Q-TOF LC/MS · LC-ESI-QTOF · NEGATIVE)
- Other MSMassBank of North America (MoNA) (Orbitrap · negative) · MassBank of North America (MoNA) (ESI · negative)
- FTIRSpectraBase (KBr WAFER)
Experimental spectra held by these sources; each link opens the source's own record.
Literature
Reading PubChem, OpenAlex and GSRS…
Bioactivity
Reading ChEMBL…
References
- [1]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
- [2]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
- [3]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
- [4]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
- [5]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
- ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
- ·Literature on PubChem
Data last updated 2026-10-14.