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Showing metabocard for Methyloxirane (HMDB0031558)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:44:03 UTC
Update Date2023-02-21 17:20:49 UTC
HMDB IDHMDB0031558
Secondary Accession Numbers
  • HMDB31558
Metabolite Identification
Common NameMethyloxirane
DescriptionMethyloxirane, also known as 2,3-epoxypropane or propylene oxide, belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms). Methyloxirane is a sweet and ethereal tasting compound. Methyloxirane is a potentially toxic compound.
Structure
Data?1677000049
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031558 (Methyloxirane)


  Mrv1652305271900212D          

  4  4  0  0  0  0            999 V2000
    0.2382    1.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    0.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743    0.1743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  4  3  1  0  0  0  0
M  END
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3D MOL for HMDB0031558 (Methyloxirane)

HMDB0031558
     RDKit          3D
Methyloxirane
 10 10  0  0  0  0  0  0  0  0999 V2000
   -1.2457   -0.0629   -0.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1384   -0.3066    0.1140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3377    0.1377   -0.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7644    0.9778    0.5202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3262    0.5258   -1.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7830    0.5199    0.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7452   -1.0662   -0.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2165   -1.0827    0.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3045   -0.2706   -0.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3387    0.6278   -1.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  2  1  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  2  8  1  0
  3  9  1  0
  3 10  1  0
M  END
Download

3D SDF for HMDB0031558 (Methyloxirane)


  Mrv1652305271900212D          

  4  4  0  0  0  0            999 V2000
    0.2382    1.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6507    0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2382    0.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1743    0.1743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  4  3  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031558

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CO1

> <INCHI_IDENTIFIER>
InChI=1S/C3H6O/c1-3-2-4-3/h3H,2H2,1H3

> <INCHI_KEY>
GOOHAUXETOMSMM-UHFFFAOYSA-N

> <FORMULA>
C3H6O

> <MOLECULAR_WEIGHT>
58.0791

> <EXACT_MASS>
58.041864814

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
6.333758711147767

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methyloxirane

> <ALOGPS_LOGP>
0.04

> <JCHEM_LOGP>
0.36959951633333327

> <ALOGPS_LOGS>
0.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.176651995436523

> <JCHEM_POLAR_SURFACE_AREA>
12.53

> <JCHEM_REFRACTIVITY>
15.462299999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.01e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
propylene oxide

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0031558 (Methyloxirane)

HMDB0031558
     RDKit          3D
Methyloxirane
 10 10  0  0  0  0  0  0  0  0999 V2000
   -1.2457   -0.0629   -0.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1384   -0.3066    0.1140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3377    0.1377   -0.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7644    0.9778    0.5202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3262    0.5258   -1.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7830    0.5199    0.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7452   -1.0662   -0.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2165   -1.0827    0.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3045   -0.2706   -0.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3387    0.6278   -1.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  2  1  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  2  8  1  0
  3  9  1  0
  3 10  1  0
M  END
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PDB for HMDB0031558 (Methyloxirane)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       0.445   3.199   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.215   0.325   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.445   1.659   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.325   0.325   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    3    4                                                       
CONECT    3    1    2    4                                                  
CONECT    4    2    3                                                       
MASTER        0    0    0    0    0    0    0    0    4    0    8    0
END
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3D PDB for HMDB0031558 (Methyloxirane)

COMPND    HMDB0031558
HETATM    1  C1  UNL     1      -1.246  -0.063  -0.375  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.138  -0.307   0.114  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.338   0.138  -0.539  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.764   0.978   0.520  1.00  0.00           O  
HETATM    5  H1  UNL     1      -1.326   0.526  -1.290  1.00  0.00           H  
HETATM    6  H2  UNL     1      -1.783   0.520   0.430  1.00  0.00           H  
HETATM    7  H3  UNL     1      -1.745  -1.066  -0.496  1.00  0.00           H  
HETATM    8  H4  UNL     1       0.216  -1.083   0.906  1.00  0.00           H  
HETATM    9  H5  UNL     1       2.305  -0.271  -0.178  1.00  0.00           H  
HETATM   10  H6  UNL     1       1.339   0.628  -1.535  1.00  0.00           H  
CONECT    1    2    5    6    7
CONECT    2    3    4    8
CONECT    3    4    9   10
END
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SMILES for HMDB0031558 (Methyloxirane)

CC1CO1
Download

INCHI for HMDB0031558 (Methyloxirane)

InChI=1S/C3H6O/c1-3-2-4-3/h3H,2H2,1H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1,2-Propylene oxideChEBI
2,3-EpoxypropaneChEBI
EpoxypropaneChEBI
MethyloxacyclopropaneChEBI
Propylene oxideChEBI
(+/-)-methyloxiraneHMDB
(+/-)-propylene oxideHMDB
(S)-(-)-Propylene oxideHMDB
1,2-Epoxy-propaneHMDB
1,2-EpoxypropaneHMDB
2-Methyl oxiraneHMDB
2-Methyl-oxiraneHMDB
2-MethyloxiranHMDB
2-MethyloxiraneHMDB
3-Methyl-1,2-epoxypropaneHMDB
AD 6 (suspending agent)HMDB
EpihydrinHMDB
Epoxy-propaneHMDB
Methyl ethylene oxideHMDB
Methyl oxiraneHMDB
Methyl-(S)-oxiraneHMDB
Methyl-ethylene oxideHMDB
Methyl-oxiraneHMDB
Methylethylene oxideHMDB
Oxyde de propyleneHMDB
Propene oxideHMDB
Propylene epoxideHMDB
PropyleneoxideHMDB
S(-)-MethyloxiraneHMDB
Propene epoxideHMDB
MethyloxiraneChEBI
Chemical FormulaC3H6O
Average Molecular Weight58.0791
Monoisotopic Molecular Weight58.041864814
IUPAC Name2-methyloxirane
Traditional Namepropylene oxide
CAS Registry Number75-56-9
SMILES
CC1CO1
InChI Identifier
InChI=1S/C3H6O/c1-3-2-4-3/h3H,2H2,1H3
InChI KeyGOOHAUXETOMSMM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassEpoxides
Sub ClassNot Available
Direct ParentEpoxides
Alternative Parents
Substituents
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
ProcessNot Available
Role
Environmental roleIndustrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-111.9 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility590 mg/mL at 25 °CNot Available
LogP0.03Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility201 g/LALOGPS
logP0.04ALOGPS
logP0.37ChemAxon
logS0.54ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity15.46 m³·mol⁻¹ChemAxon
Polarizability6.33 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+120.53730932474
DeepCCS[M-H]-118.64130932474
DeepCCS[M-2H]-154.0230932474
DeepCCS[M+Na]+128.21930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MethyloxiraneCC1CO1656.3Standard polar33892256
MethyloxiraneCC1CO1453.8Standard non polar33892256
MethyloxiraneCC1CO1461.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Methyloxirane EI-B (Non-derivatized)splash10-002f-9000000000-3f05d968e40f8eacf7e22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyloxirane EI-B (Non-derivatized)splash10-002f-9000000000-3f05d968e40f8eacf7e22018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyloxirane GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9000000000-14a67668e01cd34da6f52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyloxirane GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-9000000000-75c4313f7dba690a8a682014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyloxirane 10V, Positive-QTOFsplash10-0a4i-9000000000-2809da7584a192d3c9522016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyloxirane 20V, Positive-QTOFsplash10-0a4l-9000000000-e04a808a6c7ea551fe072016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyloxirane 40V, Positive-QTOFsplash10-0006-9000000000-6d95bc4ff8c653f744402016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyloxirane 10V, Negative-QTOFsplash10-0a4i-9000000000-f6193463d18cb059b7062016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyloxirane 20V, Negative-QTOFsplash10-0a4i-9000000000-fe386cbd774acc3341102016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyloxirane 40V, Negative-QTOFsplash10-0006-9000000000-ba65edaf304df379c2ba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyloxirane 10V, Negative-QTOFsplash10-0a4i-9000000000-6e3379842f4da69e8e2b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyloxirane 20V, Negative-QTOFsplash10-0a4i-9000000000-45e03d09a7c1ac5eac002021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyloxirane 40V, Negative-QTOFsplash10-052f-9000000000-9d4ef0a746c7edc8e9922021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyloxirane 10V, Positive-QTOFsplash10-052f-9000000000-7f5c1c6cb93e5f3b85bb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyloxirane 20V, Positive-QTOFsplash10-052f-9000000000-337a1ac0d8b7e346c5182021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyloxirane 40V, Positive-QTOFsplash10-000f-9000000000-440ea18042dc425b6ae32021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008171
KNApSAcK IDC00012262
Chemspider ID6138
KEGG Compound IDC15508
BioCyc ID12-EPOXYPROPANE
BiGG IDNot Available
Wikipedia LinkPropylene_oxide
METLIN IDNot Available
PubChem Compound6378
PDB IDNot Available
ChEBI ID38685
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Boyd JM, Clark DD, Kofoed MA, Ensign SA: Mechanism of inhibition of aliphatic epoxide carboxylation by the coenzyme M analog 2-bromoethanesulfonate. J Biol Chem. 2010 Aug 13;285(33):25232-42. doi: 10.1074/jbc.M110.144410. Epub 2010 Jun 15. [PubMed:20551308 ]
  2. Chen LJ, Lebetkin EH, Nwakpuda EI, Burka LT: Metabolism and disposition of n-butyl glycidyl ether in F344 rats and B6C3F1 mice. Drug Metab Dispos. 2007 Dec;35(12):2218-24. Epub 2007 Sep 17. [PubMed:17875671 ]
  3. Li Y, Li P, Xiao HB, Hu D, Yuan CY: [Detonation temperature measurement of epoxypropane using instantaneous spectrum method]. Guang Pu Xue Yu Guang Pu Fen Xi. 2008 Mar;28(3):490-3. [PubMed:18536396 ]
  4. Qian SH, Xiang LJ, Deng HB, Xiao M, Lin H, Li XQ: [Preconcentration of trace Pd (II) on crosslinked chitosan and determination by graphite furnace atomic absorption spectrometry]. Guang Pu Xue Yu Guang Pu Fen Xi. 2007 Mar;27(3):592-4. [PubMed:17554930 ]
  5. Kim KN, Ko YJ, Kang MC, Yang HM, Roh SW, Oda T, Jeon YJ, Jung WK, Heo SJ, Yoon WJ, Kim D: Anti-inflammatory effects of trans-1,3-diphenyl-2,3-epoxypropane-1-one mediated by suppression of inflammatory mediators in LPS-stimulated RAW 264.7 macrophages. Food Chem Toxicol. 2013 Mar;53:371-5. doi: 10.1016/j.fct.2012.12.021. Epub 2012 Dec 21. [PubMed:23266270 ]
  6. Krishnakumar AM, Sliwa D, Endrizzi JA, Boyd ES, Ensign SA, Peters JW: Getting a handle on the role of coenzyme M in alkene metabolism. Microbiol Mol Biol Rev. 2008 Sep;72(3):445-56. doi: 10.1128/MMBR.00005-08. [PubMed:18772284 ]
  7. Sliwa DA, Krishnakumar AM, Peters JW, Ensign SA: Molecular basis for enantioselectivity in the (R)- and (S)-hydroxypropylthioethanesulfonate dehydrogenases, a unique pair of stereoselective short-chain dehydrogenases/reductases involved in aliphatic epoxide carboxylation. Biochemistry. 2010 Apr 27;49(16):3487-98. doi: 10.1021/bi100294m. [PubMed:20302306 ]
  8. Dai R, Nie X, Li H, Saeed MK, Deng Y, Yao G: Investigation of beta-CD-derivatized erythromycin as chiral selector in CE. Electrophoresis. 2007 Aug;28(15):2566-72. [PubMed:17577196 ]
  9. Zhao Y, Truhlar DG: How well can new-generation density functionals describe protonated epoxides where older functionals fail? J Org Chem. 2007 Jan 5;72(1):295-8. [PubMed:17194116 ]
  10. Olender D, Zwawiak J, Lukianchuk V, Lesyk R, Kropacz A, Fojutowski A, Zaprutko L: Synthesis of some N-substituted nitroimidazole derivatives as potential antioxidant and antifungal agents. Eur J Med Chem. 2009 Feb;44(2):645-52. doi: 10.1016/j.ejmech.2008.05.016. Epub 2008 May 28. [PubMed:18590938 ]
  11. Luo MF, Wu H, Wang L, Xing XH: [Study on the structure and function of a stable methane-oxidizing mixed microbial consortium]. Wei Sheng Wu Xue Bao. 2007 Feb;47(1):103-9. [PubMed:17436634 ]
  12. Li P, Hu D, Yuan CY, Dai SH, Xiao HB: [Using instantaneous spectra to determine dominant species in the DDT process of epoxypropane]. Guang Pu Xue Yu Guang Pu Fen Xi. 2006 Sep;26(9):1569-72. [PubMed:17112018 ]
  13. Karmali PP, Chao Y, Park JH, Sailor MJ, Ruoslahti E, Esener SC, Simberg D: Different effect of hydrogelation on antifouling and circulation properties of dextran-iron oxide nanoparticles. Mol Pharm. 2012 Mar 5;9(3):539-45. doi: 10.1021/mp200375x. Epub 2012 Feb 2. [PubMed:22243419 ]
  14. Mao W, Zangerl AR, Berenbaum MR, Schuler MA: Metabolism of myristicin by Depressaria pastinacella CYP6AB3v2 and inhibition by its metabolite. Insect Biochem Mol Biol. 2008 Jun;38(6):645-51. doi: 10.1016/j.ibmb.2008.03.013. Epub 2008 Apr 9. [PubMed:18510976 ]
  15. Owens CR, Karceski JK, Mattes TE: Gaseous alkene biotransformation and enantioselective epoxyalkane formation by Nocardioides sp. strain JS614. Appl Microbiol Biotechnol. 2009 Sep;84(4):685-92. doi: 10.1007/s00253-009-2019-3. Epub 2009 May 9. [PubMed:19430773 ]
  16. Rizzo A, Vahtras O: Ab initio study of excited state electronic circular dichroism. Two prototype cases: methyl oxirane and R-(+)-1,1'-bi(2-naphthol). J Chem Phys. 2011 Jun 28;134(24):244109. doi: 10.1063/1.3602219. [PubMed:21721614 ]
  17. Li SJ, Sun YL, Hu DD, Chen C, Cui YL: [Preparation of metal chelate affinity chromatographic medium and its application in the purification of 6 x histidine-tagged protein]. Sheng Wu Gong Cheng Xue Bao. 2007 Sep;23(5):941-6. [PubMed:18051879 ]
  18. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .