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Identification
YMDB IDYMDB00676
NameCaprylic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionCaprylic acid, also known as 8:0 or octylic acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Caprylic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Caprylic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 0ctanoic acid
  • 1-Heptanecarboxylate
  • 1-Heptanecarboxylic acid
  • 1-octanoic acid
  • 8-[(1R,2R)-3-Oxo-2-{(Z)-pent-2-enyl}cyclopentyl]octanoate
  • Acide octanoique
  • Acido octanoico
  • Acidum octanocium
  • C-8 Acid
  • C8:0
  • Caprylate
  • Caprylic acid
  • capryloate
  • Caprylsaeure
  • CH3-[CH2]6-COOH
  • Enantic acid
  • Heptane-1-carboxylic acid
  • Kaprylsaeure
  • Kyselina kaprylova
  • n-Caprylate
  • n-Caprylic acid
  • n-Octanoate
  • n-Octanoic acid
  • n-Octoate
  • n-Octoic acid
  • n-Octylate
  • n-Octylic acid
  • octanoate
  • Octanoic acid
  • octanoic acid, ion(1-)
  • Octansaeure
  • Octic acid
  • octoic acid
  • Octylate
  • octylic acid
  • 8:0
  • Acidum octanoicum
  • OCTANOIC ACID (caprylIC ACID)
  • OCTANOate (caprylate)
  • Octoate
  • Emery 657
  • Kortacid 0899
  • Lunac 8-95
  • Lunac 8-98
  • Neo-fat 8
  • Neo-fat 8S
  • Prifac 2901
  • Caprylic acid, cadmium salt
  • Caprylic acid, cesium salt
  • Caprylic acid, manganese salt
  • Caprylic acid, nickel(+2) salt
  • Caprylic acid, zinc salt
  • Caprylic acid, aluminum salt
  • Caprylic acid, barium salt
  • Caprylic acid, chromium(+2) salt
  • Caprylic acid, lead(+2) salt
  • Caprylic acid, potassium salt
  • Caprylic acid, tin(+2) salt
  • Sodium octanoate
  • Caprylic acid, 14C-labeled
  • Caprylic acid, lithium salt
  • Caprylic acid, ruthenium(+3) salt
  • Caprylic acid, sodium salt
  • Caprylic acid, sodium salt, 11C-labeled
  • Caprylic acid, tin salt
  • Caprylic acid, zirconium salt
  • Sodium caprylate
  • Caprylic acid, ammonia salt
  • Caprylic acid, calcium salt
  • Caprylic acid, cobalt salt
  • Caprylic acid, copper salt
  • Caprylic acid, copper(+2) salt
  • Caprylic acid, iridum(+3) salt
  • Caprylic acid, iron(+3) salt
  • Caprylic acid, lanthanum(+3) salt
  • Caprylic acid, zirconium(+4) salt
  • FA(8:0)
  • Lithium octanoate
CAS number124-07-2
WeightAverage: 144.2114
Monoisotopic: 144.115029756
InChI KeyWWZKQHOCKIZLMA-UHFFFAOYSA-N
InChIInChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)
IUPAC Nameoctanoic acid
Traditional IUPAC Namecaprylic acid
Chemical FormulaC8H16O2
SMILESCCCCCCCC(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Charge0
Melting point16.5 °C
Experimental Properties
PropertyValueReference
Water Solubility0.789 mg/mL at 30 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP3.05 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.91 g/LALOGPS
logP2.92ALOGPS
logP2.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)5.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity40.28 m³·mol⁻¹ChemAxon
Polarizability17.4 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • cell envelope
  • mitochondrion
  • endoplasmic reticulum
  • lipid particle
  • peroxisome
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
CheeseFDB003336
CheesyFDB003336
FattyFDB003336
OilyFDB003336
RancidFDB003336
SweatFDB003336
VegetableFDB003336
WaxyFDB003336
SMPDB Pathways
Fatty acid biosynthesisPW002458 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Fatty acid biosynthesisec00061 Map00061
alpha-Linolenic acid metabolismec00592 Map00592
SMPDB Reactions
Caprylic acid + Malonate3-Oxodecanoic acid
trans-2-Octenoic acidCaprylic acid
KEGG Reactions
malonyl-CoA + Caprylic acid + hydron + NADPHcapric acid + Carbon dioxide + NADP + water + Coenzyme A
hydron + NADPH + Acetyl-CoA + malonyl-CoAwater + NADP + Carbon dioxide + Coenzyme A + Caprylic acid
Adenosine triphosphate + Caprylic acid + Coenzyme AAdenosine monophosphate + Pyrophosphate + octanoyl-CoA
water + octanoyl-CoACaprylic acid + hydron + Coenzyme A
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0159-0910000000-e609d5de69ede6fbcde0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0gb9-1920000000-1dc6ed976e003f99e23dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03kc-9000000000-74cfce03769b41313952JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0uyi-0931100000-7668e36e436054042b5cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-0910000000-e609d5de69ede6fbcde0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gb9-1920000000-1dc6ed976e003f99e23dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0910000000-9ecb4ccb46e89710f76aJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0596-9100000000-8854c56056d8d3405087JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-062l-9100000000-67da39159980b9078fabJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0006-0900000000-bb237630bedcee6145d1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-2900000000-98284f50a271878c8481JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-5900000000-209fbbacd4996b9a770dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-03kc-9000000000-74cfce03769b41313952JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-e2c4dff10393086340f7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-1900000000-bbde8564b4e5543a636aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-Q-Exactive Plus , Negativesplash10-0006-0900000000-d219a0c6559a4783fd81JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-e2c4dff10393086340f7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-1900000000-bbde8564b4e5543a636aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0006-0900000000-ca22ecd0b25fa371fc73JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-2900000000-ac7c80e50c93b8cc3af7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9400000000-d2694b5f89d8eaeb2ab1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-f2b24072c91d8b0e4078JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-ad62d44e72f4dd1760abJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-7900000000-9c869b84815f21dffc7cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-b8a648d443695914e479JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-03kc-9000000000-8c7db9a9d75b2cc1bd1cJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Furukawa, K., Yamada, T., Mizoguchi, H., Hara, S. (2003). "Increased ethyl caproate production by inositol limitation in Saccharomyces cerevisiae." J Biosci Bioeng 95:448-454.16233438
  • Antonelli, A., Castellari, L., Zambonelli, C., Carnacini, A. (1999). "Yeast influence on volatile composition of wines." J Agric Food Chem 47:1139-1144.10552428
  • Tsakiris, A., Koutinas, A. A., Psarianos, C., Kourkoutas, Y., Bekatorou, A. (2010). "A new process for wine production by penetration of yeast in uncrushed frozen grapes." Appl Biochem Biotechnol 162:1109-1121.20151225
  • Patel, S., Shibamoto, T. (2002). "Effect of different strains of Saccharomyces cerevisiae on production of volatiles in Napa Gamay wine and Petite Sirah wine." J Agric Food Chem 50:5649-5653.12236692
  • Kogan, G. L., Filipp, D., Arman, I. P., Leibovich, B. A., Beliaeva, E. S. (1991). "[Cloning of segments of the Drosophila melanogaster genome using artificial chromosomes of the yeast Saccharomyces cerevisiae]." Genetika 27:1316-1323.1761208
Synthesis Reference:Caprylic acid. Jpn. Kokai Tokkyo Koho (1983), 4 pp.
External Links:
ResourceLink
CHEBI ID28837
HMDB IDHMDB00482
Pubchem Compound ID379
Kegg IDC06423
ChemSpider ID370
FOODB IDFDB003336
WikipediaCaprylic_acid
BioCyc IDCPD-195

Enzymes

General function:
Involved in catalytic activity
Specific function:
Esterification, concomitant with transport, of endogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. Preferentially acts on C9:0-C13:0 fatty acids although C7:0-C17:0 fatty acids are tolerated
Gene Name:
FAA2
Uniprot ID:
P39518
Molecular weight:
83437.10156
Reactions
ATP + a long-chain carboxylic acid + CoA → AMP + diphosphate + an acyl-CoA.
General function:
Involved in transferase activity
Specific function:
Fatty acid synthetase catalyzes the formation of long- chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. The beta subunit contains domains for:[acyl-carrier-protein] acetyltransferase and malonyltransferase, S-acyl fatty acid synthase thioesterase, enoyl-[acyl-carrier-protein] reductase, and 3-hydroxypalmitoyl-[acyl-carrier-protein] dehydratase
Gene Name:
FAS1
Uniprot ID:
P07149
Molecular weight:
228689.0
Reactions
Acetyl-CoA + n malonyl-CoA + 2n NADH + 2n NADPH → long-chain-acyl-CoA + n CoA + n CO(2) + 2n NAD(+) + 2n NADP(+).
Acetyl-CoA + [acyl-carrier-protein] → CoA + acetyl-[acyl-carrier-protein].
Malonyl-CoA + [acyl-carrier-protein] → CoA + malonyl-[acyl-carrier-protein].
(3R)-3-hydroxypalmitoyl-[acyl-carrier-protein] → hexadec-2-enoyl-[acyl-carrier-protein] + H(2)O.
Acyl-[acyl-carrier-protein] + NAD(+) → trans-2,3-dehydroacyl-[acyl-carrier-protein] + NADH.
Oleoyl-[acyl-carrier-protein] + H(2)O → [acyl-carrier-protein] + oleate.
General function:
Involved in acyl-CoA thioesterase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH
Gene Name:
TES1
Uniprot ID:
P41903
Molecular weight:
40259.39844
Reactions
Palmitoyl-CoA + H(2)O → CoA + palmitate.