Caprylic acid (YMDB00676)

Identification

YMDB ID

YMDB00676

Name

Caprylic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Caprylic acid, also known as octanoate or 8:0, 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

MOL SDF PDB SMILES InChI

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 number

124-07-2

Weight

Average: 144.2114
Monoisotopic: 144.115029756

InChI Key

WWZKQHOCKIZLMA-UHFFFAOYSA-N

InChI

InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)

IUPAC Name

octanoic acid

Traditional IUPAC Name

caprylic acid

Chemical Formula

C₈H₁₆O₂

SMILES

CCCCCCCC(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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-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 Framework

Aliphatic acyclic compounds

External Descriptors

medium-chain fatty acid (CHEBI:28837 )
straight-chain saturated fatty acid (CHEBI:28837 )
Straight chain fatty acids (C06423 )
Saturated fatty acids (C06423 )
Straight chain fatty acids (LMFA01010008 )

Physical Properties

State

Liquid

Charge

Melting point

16.5 °C

Experimental Properties

Property	Value	Reference
Water Solubility	0.789 mg/mL at 30 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	3.05 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.91 g/L	ALOGPS
logP	2.92	ALOGPS
logP	2.7	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	5.19	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	40.28 m³·mol⁻¹	ChemAxon
Polarizability	17.4 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

extracellular
cell envelope
mitochondrion
endoplasmic reticulum
lipid particle
peroxisome
cytoplasm

Organoleptic Properties

Flavour/Odour	Source
Cheese	FDB003336
Cheesy	FDB003336
Fatty	FDB003336
Oily	FDB003336
Rancid	FDB003336
Sweat	FDB003336
Vegetable	FDB003336
Waxy	FDB003336

SMPDB Pathways

Fatty acid biosynthesis

PW002458

KEGG Pathways

Fatty acid biosynthesis	ec00061
alpha-Linolenic acid metabolism	ec00592

SMPDB Reactions

Caprylic acid + Malonate → 3-Oxodecanoic acid

trans-2-Octenoic acid → Caprylic acid

KEGG Reactions

malonyl-CoA + Caprylic acid + hydron + NADPH → capric acid + Carbon dioxide + NADP + water + Coenzyme A

hydron + NADPH + Acetyl-CoA + malonyl-CoA → water + NADP + Carbon dioxide + Coenzyme A + Caprylic acid

Adenosine triphosphate + Caprylic acid + Coenzyme A ↔ Adenosine monophosphate + Pyrophosphate + octanoyl-CoA

water + octanoyl-CoA → Caprylic acid + hydron + Coenzyme A

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0159-0910000000-e609d5de69ede6fbcde0	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0gb9-1920000000-1dc6ed976e003f99e23d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03kc-9000000000-74cfce03769b41313952	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0uyi-0931100000-7668e36e436054042b5c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-0910000000-e609d5de69ede6fbcde0	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0gb9-1920000000-1dc6ed976e003f99e23d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0910000000-9ecb4ccb46e89710f76a	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0596-9100000000-8854c56056d8d3405087	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-062l-9100000000-67da39159980b9078fab	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0006-0900000000-bb237630bedcee6145d1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0006-2900000000-98284f50a271878c8481	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0006-5900000000-209fbbacd4996b9a770d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-03kc-9000000000-74cfce03769b41313952	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-0900000000-e2c4dff10393086340f7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0006-1900000000-bbde8564b4e5543a636a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-Q-Exactive Plus , Negative	splash10-0006-0900000000-d219a0c6559a4783fd81	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0900000000-e2c4dff10393086340f7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-1900000000-bbde8564b4e5543a636a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0006-0900000000-ca22ecd0b25fa371fc73	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0gvp-9100000000-58c00a2024ba0bae4ff4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9300000000-2505e6738cf5d5877654	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-1ab4cdf8f74c93312743	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-2900000000-ac7c80e50c93b8cc3af7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9400000000-d2694b5f89d8eaeb2ab1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-f2b24072c91d8b0e4078	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-1900000000-ad62d44e72f4dd1760ab	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0007-7900000000-9c869b84815f21dffc7c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-b8a648d443695914e479	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6u-9100000000-f5c38fdad70b324e75ac	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-bee103956686b4840d1e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-e7cbd036c8e80018c825	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-8f2b048da6331570976c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-cd31ca01a5fa6be86acb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9100000000-682c215be5abe1fe87ed	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-03kc-9000000000-8c7db9a9d75b2cc1bd1c	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	28837
HMDB ID	HMDB00482
Pubchem Compound ID	379
Kegg ID	C06423
ChemSpider ID	370
FOODB ID	FDB003336
Wikipedia	Caprylic_acid
BioCyc ID	CPD-195

Enzymes

Protein Details

1. Long-chain-fatty-acid--CoA ligase 2

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.

Protein Details

2. Fatty acid synthase subunit beta

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.

Protein Details

3. Peroxisomal acyl-coenzyme A thioester hydrolase 1

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.

Structure for #<Compound:0xa6ef3b24>

Enzymes

Reactions

Reactions

Reactions