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Showing metabocard for 1,3-Benzenediol (HMDB0032037)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:47:23 UTC
Update Date2023-02-21 17:21:30 UTC
HMDB IDHMDB0032037
Secondary Accession Numbers
  • HMDB32037
Metabolite Identification
Common Name1,3-Benzenediol
Description1,3-Benzenediol, also known as resorcin or m-hydroquinone, belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3. 1,3-Benzenediol exists in all living organisms, ranging from bacteria to humans. 1,3-Benzenediol is a creamy, hawthorn, and musty tasting compound. 1,3-Benzenediol has been detected, but not quantified, in several different foods, such as alcoholic beverages, cereals and cereal products, coffee and coffee products, eggplants, and java plums. This could make 1,3-benzenediol a potential biomarker for the consumption of these foods. 1,3-Benzenediol is a potentially toxic compound. In addition, exogenous ochronosis is associated with prolonged exposure to resorcinol . Data regarding the specific mechanisms of action of resorcinol does not appear to be readily accessible in the literature. Nevertheless, the role played by iodide ions in the irreversible inactivation of the enzymes is not yet fully elucidated . Resorcinol works by helping to remove hard, scaly, or roughened skin. In particular, it appears that resorcinol indicated for treating acne, dermatitis, or eczema in various skin care topical applications and peels revolves around the compound's ability to precipitate cutaneous proteins from the treated skin . In LPO and TPO, the resulting π-cation radical of the porphyrin can isomerize to a radical cation with the radical in an aromatic side chain of the enzyme . In vitro and in vivo studies have demonstrated that resorcinol can inhibit peroxidases in the thyroid and subsequently block the synthesis of thyroid hormones and cause goiter .
Structure
Data?1677000090
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0032037 (1,3-Benzenediol)


  Mrv1652305062021452D          

  8  8  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  2  1  2  0  0  0  0
  7  5  2  0  0  0  0
  4  7  1  0  0  0  0
  3  4  2  0  0  0  0
  2  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
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3D MOL for HMDB0032037 (1,3-Benzenediol)

HMDB0032037
     RDKit          3D
1,3-Benzenediol
 14 14  0  0  0  0  0  0  0  0999 V2000
    2.5221   -1.0435   -0.1394 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2714   -0.4210   -0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1569    0.9524   -0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0791    1.5633   -0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2562    0.8312   -0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1264   -0.5423    0.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2824   -1.3128    0.0786 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1039   -1.1505   -0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9774   -1.2193    0.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0756    1.5327   -0.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1676    2.6406   -0.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2213    1.3203   -0.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1965   -0.9189    0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2222   -2.2322    0.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  2  1  0
  1  9  1  0
  3 10  1  0
  4 11  1  0
  5 12  1  0
  7 13  1  0
  8 14  1  0
M  END
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3D SDF for HMDB0032037 (1,3-Benzenediol)


  Mrv1652305062021452D          

  8  8  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  2  1  2  0  0  0  0
  7  5  2  0  0  0  0
  4  7  1  0  0  0  0
  3  4  2  0  0  0  0
  2  3  1  0  0  0  0
  6  3  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032037

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC(O)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H6O2/c7-5-2-1-3-6(8)4-5/h1-4,7-8H

> <INCHI_KEY>
GHMLBKRAJCXXBS-UHFFFAOYSA-N

> <FORMULA>
C6H6O2

> <MOLECULAR_WEIGHT>
110.1106

> <EXACT_MASS>
110.036779436

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
10.74786583441956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
benzene-1,3-diol

> <ALOGPS_LOGP>
0.70

> <JCHEM_LOGP>
1.3661151726666665

> <ALOGPS_LOGS>
-0.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.725686553960157

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.26428499493661

> <JCHEM_PKA_STRONGEST_BASIC>
-5.663505847935281

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
30.019799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.23e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
resorcinol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0032037 (1,3-Benzenediol)

HMDB0032037
     RDKit          3D
1,3-Benzenediol
 14 14  0  0  0  0  0  0  0  0999 V2000
    2.5221   -1.0435   -0.1394 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2714   -0.4210   -0.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1569    0.9524   -0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0791    1.5633   -0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2562    0.8312   -0.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1264   -0.5423    0.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2824   -1.3128    0.0786 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1039   -1.1505   -0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9774   -1.2193    0.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0756    1.5327   -0.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1676    2.6406   -0.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2213    1.3203   -0.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1965   -0.9189    0.1049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2222   -2.2322    0.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  2  1  0
  1  9  1  0
  3 10  1  0
  4 11  1  0
  5 12  1  0
  7 13  1  0
  8 14  1  0
M  END
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PDB for HMDB0032037 (1,3-Benzenediol)

HEADER    PROTEIN                                 06-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-20         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000   3.080   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
CONECT    1    5    2                                                       
CONECT    2    1    3                                                       
CONECT    3    4    2    6                                                  
CONECT    4    7    3                                                       
CONECT    5    1    7                                                       
CONECT    6    3                                                            
CONECT    7    5    4    8                                                  
CONECT    8    7                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for HMDB0032037 (1,3-Benzenediol)

COMPND    HMDB0032037
HETATM    1  O1  UNL     1       2.522  -1.043  -0.139  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.271  -0.421  -0.106  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.157   0.952  -0.148  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.079   1.563  -0.115  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.256   0.831  -0.039  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.126  -0.542   0.002  1.00  0.00           C  
HETATM    7  O2  UNL     1      -2.282  -1.313   0.079  1.00  0.00           O  
HETATM    8  C6  UNL     1       0.104  -1.151  -0.031  1.00  0.00           C  
HETATM    9  H1  UNL     1       2.977  -1.219   0.762  1.00  0.00           H  
HETATM   10  H2  UNL     1       2.076   1.533  -0.208  1.00  0.00           H  
HETATM   11  H3  UNL     1      -0.168   2.641  -0.148  1.00  0.00           H  
HETATM   12  H4  UNL     1      -2.221   1.320  -0.014  1.00  0.00           H  
HETATM   13  H5  UNL     1      -3.196  -0.919   0.105  1.00  0.00           H  
HETATM   14  H6  UNL     1       0.222  -2.232   0.001  1.00  0.00           H  
CONECT    1    2    9
CONECT    2    3    3    8
CONECT    3    4   10
CONECT    4    5    5   11
CONECT    5    6   12
CONECT    6    7    8    8
CONECT    7   13
CONECT    8   14
END
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SMILES for HMDB0032037 (1,3-Benzenediol)

OC1=CC(O)=CC=C1
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INCHI for HMDB0032037 (1,3-Benzenediol)

InChI=1S/C6H6O2/c7-5-2-1-3-6(8)4-5/h1-4,7-8H
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1,3-DihydroxybenzeneChEBI
1,3-DihydroxybenzolChEBI
m-HydroquinoneChEBI
m-HydroxyphenolChEBI
ResorcinChEBI
ResorzinChEBI
Resorcinol disodium saltMeSH
Resorcinol, monocopper (2+) saltMeSH
1,3-BenzenediolChEBI
1,3-Dihydroxy-benzeneHMDB
3-HydroxyphenolHMDB
FEMA 3589HMDB
m-BenzenediolHMDB
m-DihydroxybenzeneHMDB
m-DioxybenzeneHMDB
m-Hydroxy-phenolHMDB
Resorcinol, 8ciHMDB
RezorsineHMDB
Benzene-1,3-DiolHMDB
ResorcinolHMDB
Chemical FormulaC6H6O2
Average Molecular Weight110.1106
Monoisotopic Molecular Weight110.036779436
IUPAC Namebenzene-1,3-diol
Traditional Nameresorcinol
CAS Registry Number108-46-3
SMILES
OC1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C6H6O2/c7-5-2-1-3-6(8)4-5/h1-4,7-8H
InChI KeyGHMLBKRAJCXXBS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentResorcinols
Alternative Parents
Substituents
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationEnvironmental role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point111 °CNot Available
Boiling Point178.00 °C. @ 16.00 mm HgThe Good Scents Company Information System
Water Solubility717 mg/mL at 25 °CNot Available
LogP0.80Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility82.3 g/LALOGPS
logP0.7ALOGPS
logP1.37ChemAxon
logS-0.13ALOGPS
pKa (Strongest Acidic)9.26ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.02 m³·mol⁻¹ChemAxon
Polarizability10.75 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+120.731661259
DarkChem[M-H]-116.97731661259
DeepCCS[M+H]+120.16530932474
DeepCCS[M-H]-117.68330932474
DeepCCS[M-2H]-154.09730932474
DeepCCS[M+Na]+128.78430932474
AllCCS[M+H]+122.832859911
AllCCS[M+H-H2O]+117.832859911
AllCCS[M+NH4]+127.532859911
AllCCS[M+Na]+128.832859911
AllCCS[M-H]-117.432859911
AllCCS[M+Na-2H]-119.932859911
AllCCS[M+HCOO]-122.732859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. 2.01 minutes32390414
Predicted by Siyang on May 30, 20229.7656 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.75 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid74.9 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1042.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid346.6 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid112.0 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid224.9 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid227.1 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid407.3 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid315.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)281.2 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid725.8 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid250.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid918.2 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid246.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid292.5 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate613.3 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA330.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water202.1 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1,3-BenzenediolOC1=CC(O)=CC=C12945.5Standard polar33892256
1,3-BenzenediolOC1=CC(O)=CC=C11400.0Standard non polar33892256
1,3-BenzenediolOC1=CC(O)=CC=C11288.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1,3-Benzenediol,1TMS,isomer #1C[Si](C)(C)OC1=CC=CC(O)=C11340.1Semi standard non polar33892256
1,3-Benzenediol,2TMS,isomer #1C[Si](C)(C)OC1=CC=CC(O[Si](C)(C)C)=C11393.4Semi standard non polar33892256
1,3-Benzenediol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC(O)=C11568.6Semi standard non polar33892256
1,3-Benzenediol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C11831.1Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB11085
Phenol Explorer Compound ID663
FooDB IDFDB008738
KNApSAcK IDC00002671
Chemspider ID4878
KEGG Compound IDC01751
BioCyc IDCPD-623
BiGG IDNot Available
Wikipedia LinkResorcinol
METLIN IDNot Available
PubChem Compound5054
PDB IDRCO
ChEBI ID27810
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1009421
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
1,3-Benzenediol → 3,4,5-trihydroxy-6-(3-hydroxyphenoxy)oxane-2-carboxylic aciddetails