Amoxicillin (CED0001042)

Record Information
Version1.0
Creation Date2016-05-22 04:23:22 UTC
Update Date2026-08-19 16:17:34 UTC
Accession NumberCHEM017476
Identification
Common NameAmoxicillin
ClassSmall Molecule
Description
Amoxicillin is an organic compound with the chemical formula C16H19N3O5S and an average molecular weight of 365.40 g/mol. Amoxicillin belongs to the beta lactams, a subclass of lactams within the organic compounds. It is further classified within the superclass of organoheterocyclic compounds. In terms of biological activity, amoxicillin acts as an inhibitor of the protein target penicillin binding protein (PBP1). The compound has been identified in or released from 24 recorded sources. These include healthcare, pharmaceuticals, and veterinary products, specifically antibiotics, penicillins, and drugs for acid related disorders. It is found in aquatic systems and sediments, such as seawater, freshwater, surface water, and groundwater, as well as drinking water and water supply sources including tap water, bottled water, and desalinated water. Additionally, it is present in wastewater, sanitation, and biosolids, including wastewater treatment effluent, industrial wastewater, mine wastewater, and unspecified wastewater. Other recorded sources include marine, shipping, and aquaculture environments, specifically bilge water and ballast water, as well as appliances, HVAC, and refrigerants, such as water heaters and water coolers, along with four more sectors. Recorded exposure routes for amoxicillin include oral, intravenous, inhalation, and touch.
Contaminant Type
  • PMT
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,5R,6R)-6-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidChEBI
6-(p-Hydroxy-alpha-aminophenylacetamido)penicillanic acidChEBI
alpha-Amino-p-hydroxybenzylpenicillinChEBI
AmolinChEBI
AmopenixinChEBI
AmoxicilinaChEBI
Amoxicillin anhydrousChEBI
AmoxicillineChEBI
AmoxicillinumChEBI
AmoxycilinChEBI
AmoxycillinChEBI
AMPCChEBI
AXChEBI
ClamoxylChEBI
MoxalChEBI
p-HydroxyampicillinChEBI
(2S,5R,6R)-6-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylateGenerator
6-(p-Hydroxy-a-aminophenylacetamido)penicillanateGenerator
6-(p-Hydroxy-a-aminophenylacetamido)penicillanic acidGenerator
6-(p-Hydroxy-alpha-aminophenylacetamido)penicillanateGenerator
6-(p-Hydroxy-α-aminophenylacetamido)penicillanateGenerator
6-(p-Hydroxy-α-aminophenylacetamido)penicillanic acidGenerator
a-Amino-p-hydroxybenzylpenicillinGenerator
Α-amino-p-hydroxybenzylpenicillinGenerator
Amoxicillin trihydrateHMDB
Amoxycillin trihydrateHMDB
D-AmoxicillinHMDB
ActimoxiHMDB
Amoxicillin monopotassium saltHMDB
Amoxicillin monosodium saltHMDB
Clariana brand OF amoxicillinHMDB
PolymoxHMDB
Amoxicillin sodiumHMDB
Clamoxyl parenteralHMDB
Trihydrate, amoxicillinHMDB
Anhydrous, amoxicillinHMDB
Clamoxyl g.a.HMDB
HydroxyampicillinHMDB
Pfizer brand OF amoxicillin sodium saltHMDB
TrimoxHMDB
WymoxHMDB
Amoxicillin clariana brandHMDB
Amoxicillin, (r*)-isomerHMDB
AmoxilHMDB
G.A., clamoxylHMDB
PenamoxHMDB
SmithKline beecham brand OF amoxicillin sodium saltHMDB
Sodium, amoxicillinHMDB
Parenteral, clamoxylHMDB
6-(a-Amino-4-hydroxyphenylacetamido)penicillanic acidHMDB
6-(D-(-)-p-Hydroxy-alpha-aminobenzyl)penicillinHMDB
6-[[Amino(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 9ciHMDB
AlmodanHMDB
AmixHMDB
AmoclenHMDB
AmopenHMDB
AmoramHMDB
Amox 250 cap 250MGHMDB
Amox 500 cap 500MGHMDB
Amox S 125 sus 125mg/5MLHMDB
Amox S 250 sus 250mg/5MLHMDB
AmoxiHMDB
Amoxi-mastHMDB
AmoxicapsHMDB
Amoxicillin (anhydrous)HMDB
Amoxicillin and clavulanate potassiumHMDB
Amoxicillin pediatricHMDB
Amoxicillin(usan)HMDB
AmoxidHMDB
AmoxidenHMDB
AmoxivetHMDB
Amoxycillin, banHMDB
AmoxymedHMDB
AmritHMDB
AnemolinHMDB
Apo-amoxiHMDB
Apo-amoxi cap 250MGHMDB
Apo-amoxi cap 500MGHMDB
Apo-amoxi PWR for susp 125mg/5MLHMDB
Apo-amoxi PWR for susp 250mg/5MLHMDB
Apo-amoxi sugar freeHMDB
AspenilHMDB
AUGMENTIN '125'HMDB
AUGMENTIN '200'HMDB
AUGMENTIN '250'HMDB
AUGMENTIN '400'HMDB
AUGMENTIN '500'HMDB
AUGMENTIN '875'HMDB
AUGMENTIN es-600HMDB
BiomoxHMDB
BristamoxHMDB
BRL 2333HMDB
CemoxinHMDB
Clamoxyl (SKB)HMDB
D-(-)-alpha-Amino-p-hydroxybenzyl penicillinHMDB
D-(-)-alpha-Amino-p-hydroxybenzylpenicillinHMDB
D-(alpha-Amino-p-hydroxybenzyl)penicillinHMDB
D-2-Amino-2-(4-hydroxyphenyl)acetamidopenicillanic acidHMDB
DelacillinHMDB
DispermoxHMDB
EfpenixHMDB
FlemoxinHMDB
GalenamoxHMDB
Gen-amoxicillin 250MGHMDB
Gen-amoxicillin 500MGHMDB
HiconcilHMDB
HistocillinHMDB
IbiamoxHMDB
ImacillinHMDB
LarotidHMDB
Metafarma capsulesHMDB
Metifarma capsulesHMDB
MoxacinHMDB
MoxatagHMDB
Novamoxin cap 250MGHMDB
Novamoxin cap 500MGHMDB
Novamoxin sus 125mg/5MLHMDB
Novamoxin sus 250mg/5MLHMDB
Nu-amoxi cap 250MGHMDB
Nu-amoxi cap 500MGHMDB
Nu-amoxi sus 125/5MLHMDB
Nu-amoxi sus 250mg/5MLHMDB
OspamoxHMDB
PHL-AmoxicillinHMDB
PiramoxHMDB
PMS-AmoxicillinHMDB
PrevpacHMDB
Pro amox PWR for oral susp 125mg/5MLHMDB
Pro amox-250 cap 250MGHMDB
Pro amox-500 cap 500MGHMDB
Pro-amox-250 orl sus 250mg/5MLHMDB
R-HydroxyampicillinHMDB
RimoxallinHMDB
RobamoxHMDB
SauracillinHMDB
Sawamox PMHMDB
SumoxHMDB
UnicillinHMDB
UtimoxHMDB
VetramoxHMDB
AmoxicillinHMDB
Chemical FormulaC16H19N3O5S
Average Molecular Mass365.404 g/mol
Monoisotopic Mass365.105 g/mol
CAS Registry Number26787-78-0
IUPAC Name(2S,5R,6R)-6-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional Nameamoxicillin
SMILES[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=C(O)C=C1)C(O)=O
InChI IdentifierInChI=1S/C16H19N3O5S/c1-16(2)11(15(23)24)19-13(22)10(14(19)25-16)18-12(21)9(17)7-3-5-8(20)6-4-7/h3-6,9-11,14,20H,17H2,1-2H3,(H,18,21)(H,23,24)/t9-,10-,11+,14-/m1/s1
InChI KeyLSQZJLSUYDQPKJ-NJBDSQKTSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentPenicillins
Alternative Parents
Substituents
  • Penicillin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Phenylacetamide
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Azetidine
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Amino acid
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Primary aliphatic amine
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.96 g/LALOGPS
logP0.75ALOGPS
logP-2.3ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.23ChemAxon
pKa (Strongest Basic)7.22ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.96 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity89.5 m³·mol⁻¹ChemAxon
Polarizability35.52 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00di-1900000000-1c2ac124e627e76a25cdNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-0900000000-f1dcbada55dfb975b85fNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03xs-0859000000-8225987d1a20c14acc00Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0190000000-febb22de5b7f210e4a46Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-056u-4960000000-f3c347843d63d99418c5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0036-8900000000-eca01f197da058161684Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-007o-9800000000-cec182c5a522a2979385Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00ec-9700000000-dc767a962e9f2608b083Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00dl-9600000000-b831842a45369bb2b48cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-06r2-0589000000-9c90c12d4fbef3a04a14Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0910000000-e26fa392674b2a230233Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-1900000000-9e60140bfff56767dbecNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-1900000000-f3065ce1009dda06cf72Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03e9-2900000000-5516c0723837b4149a68Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-06s9-5900000000-cd377b53cefaa4b23c6fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03xs-0859000000-8225987d1a20c14acc00Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0036-8900000000-62bd26570eb8aae7a515Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-056u-5960000000-d19d44c39e4481d0e1b2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03e9-2900000000-f6e458dd9ce3de4c0c25Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0190000000-9c79deb14e40c1956190Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0910000000-26e374b1aeae888b2869Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-06r2-0589000000-7c0934f2d185be1dfb1aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0900000000-523cedc0fd76b45dbcd1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-1900000000-a30edcacaca01d86e4acNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-007o-9800000000-7bb1644f9c7bf05adbf5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00ec-9700000000-e39d11a8194f1361610dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-096r-1942000000-113f344b62fa2da12fa2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-08mi-2920000000-1af60e30ced839146281Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0abc-9800000000-8bfef7a27c2a9bdb662cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0091000000-5a11ce4f38e4518c703cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0391000000-55921977de48ce477471Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dl-9520000000-9f116d1f75d12afd48bfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0019000000-5839285c6942245bf97fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0gvp-0933000000-39301b45d055fcc641e5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05fr-2900000000-9f55128039a5abf8c1a1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0109000000-cb77ba46825a37a95d27Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-08ml-5934000000-3420c791a6ae2bd2758cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9500000000-fa1688cf408feb58020dNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
5724.0Log mg/kg[3200:10000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
3Irrigation waterAgriculture & land managementNot Available
27Water CoolersAppliances, HVAC & refrigerantsNot Available
43Water heatersAppliances, HVAC & refrigerantsNot Available
50GroundwaterAquatic systems & sedimentsNot Available
51Surface waterAquatic systems & sedimentsNot Available
52SeawaterAquatic systems & sedimentsNot Available
53FreshwaterAquatic systems & sedimentsNot Available
70Stormwater runoffAutomotive & urban infrastructureNot Available
88Waterproofing spraysBuilding & ConstructionNot Available
115Drinking waterDrinking water & water supplyNot Available
116Tap waterDrinking water & water supplyNot Available
117Bottled waterDrinking water & water supplyNot Available
118Desalinated waterDrinking water & water supplyNot Available
181Ballast waterMarine, shipping & aquacultureNot Available
182Bilge waterMarine, shipping & aquacultureNot Available
242Drugs for acid related disordersHealthcare, pharmaceuticals & veterinary productsNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
340PenicillinsHealthcare, pharmaceuticals & veterinary productsNot Available
468Industrial wastewaterWastewater, sanitation & biosolidsNot Available
470Wastewater treatment effluentWastewater, sanitation & biosolidsNot Available
475Mine wastewaterWastewater, sanitation & biosolidsNot Available
477Wastewater, unspecifiedWastewater, sanitation & biosolidsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
Pathways
1 pathway
Amoxicillin Drug Metabolism Action Pathway
Amoxicillin Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)95.3653
Click to view 3D structureBeta-lactamase ACC-4A4ZYU9Escherichia coliPredicted (SEA)0.233548
Beta-lactamase structureClick to view 3D structureBeta-lactamaseP00811Escherichia coli (strain K12)Predicted (SEA)3.42537
Click to view 3D structureDelta-type opioid receptorP33533Rattus norvegicusPredicted (SEA)340.435
Delta-type opioid receptor structureClick to view 3D structureDelta-type opioid receptorP41143HumansPredicted (SEA)567.832
Solute carrier family 15 member 2 structureClick to view 3D structureSolute carrier family 15 member 2Q16348HumansPredicted (SEA)29.0378
Click to view 3D structureDelta-type opioid receptorP32300Mus musculusPredicted (SEA)347.13
Click to view 3D structureSolute carrier family 22 member 6Q4U2R8HumansPredicted (SEA)5.13805
Click to view 3D structureOrganic anion transporter 3Q8TCC7HumansPredicted (SEA)3.73676
Click to view 3D structureEfflux transporterQ3S5C3Salmonella newportPredicted (SEA)0.233548
Click to view 3D structureClass C beta-lactamase CMY-36Q48435Klebsiella pneumoniaePredicted (SEA)0.233548
Click to view 3D structureMu-type opioid receptorP97266Cavia porcellusPredicted (SEA)386.132
Click to view 3D structureMu-type opioid receptorP33535Rattus norvegicusPredicted (SEA)454.484
Beta-lactamase TEM structureClick to view 3D structureBeta-lactamase TEMP62593Escherichia coliPredicted (SEA)1.94623
Click to view 3D structureKappa-type opioid receptorP41144Cavia porcellusPredicted (SEA)527.117
Mu-type opioid receptor structureClick to view 3D structureMu-type opioid receptorP35372HumansPredicted (SEA)1384.63
Click to view 3D structureSolute carrier family 15 member 2Q63424Rattus norvegicusPredicted (SEA)14.5578
Click to view 3D structureExtended-spectrum beta-lactamase PER-6D5HSX5Aeromonas allosaccharophilaPredicted (SEA)0.856341
Click to view 3D structureADC-14 proteinQ0VTR6Acinetobacter genomosp. 3Predicted (SEA)0.856341
Click to view 3D structureBeta-lactamase SHV-11Q7X575Escherichia coliPredicted (SEA)0.856341
Click to view 3D structureADC-16 proteinQ0VTR8Acinetobacter genomosp. 3Predicted (SEA)0.856341
Click to view 3D structurePER-2 beta-lactamaseA2RP81Citrobacter freundiiPredicted (SEA)0.467095
Click to view 3D structureMu-type opioid receptorP42866Mus musculusPredicted (SEA)432.764
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)292.869
Kappa-type opioid receptor structureClick to view 3D structureKappa-type opioid receptorP41145HumansPredicted (SEA)2379.23
Concentrations
Not Available
External Links
DrugBank IDDB01060
HMDB IDHMDB0015193
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAmoxicillin
Chemspider ID31006
ChEBI ID2676
PubChem Compound ID33613
Kegg Compound IDC06827
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Nina Bilandžić, Božica Solomun Kolanović, Ivana Varenina, Giampiero Scortichini, Loredana Annunziata, Matko Brstilo, Nevenka Rudan. Veterinary drug residues determination in raw milk in Croatia. Food Control. Volume 22, Issue 12, December 2011, Pages 1941-1948
2. Adams OP, Levett PN, Cruickshank JK, Prussia PR, Garriques SA, Cooper RE: Necrotizing haemorrhagic colitis caused by resistant Shigella flexneri. Report of a case. West Indian Med J. 1993 Jun;42(2):85-6.
3. Mehta A, Chopra S, Mehta P: Antibiotic inhibition of pectolytic and cellulolytic enzyme activity in two Fusarium species. Mycopathologia. 1993 Dec;124(3):185-8.
4. Drawz SM, Bonomo RA: Three decades of beta-lactamase inhibitors. Clin Microbiol Rev. 2010 Jan;23(1):160-201. doi: 10.1128/CMR.00037-09.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=10930630
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=11431418
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=11906332
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=12569987
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=12833570
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=12850488
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=16033609
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=2083978
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=24595455
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=24631718
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=24759068
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=25998949
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=27731424
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=28987997
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833