Milk Composition Database: Showing metabocard for Iso-Valeraldehyde (BMDB0006478)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

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Record Information

Version

1.0

Creation Date

2016-09-30 23:22:21 UTC

Update Date

2020-06-04 19:20:41 UTC

MCDB ID

BMDB0006478

Secondary Accession Numbers

BMDB06478

Metabolite Identification

Common Name

Iso-Valeraldehyde

Description

3-Methylbutanal, also known as isovaleraldehyde or iso-C4H9CHO, belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group. 3-Methylbutanal exists as a liquid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 3-Methylbutanal exists in all eukaryotes, ranging from yeast to humans. 3-Methylbutanal has been found to be associated with several diseases known as ulcerative colitis, crohn's disease, hepatic encephalopathy, and perillyl alcohol administration for cancer treatment; also 3-methylbutanal has been linked to the inborn metabolic disorders including celiac disease.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Methylbutyraldehyde	ChEBI
beta-Methylbutanal	ChEBI
Iso-C4H9CHO	ChEBI
Isoamyl aldehyde	ChEBI
Isopentaldehyde	ChEBI
Isovaleral	ChEBI
Isovalerylaldehyde	ChEBI
b-Methylbutanal	Generator
Β-methylbutanal	Generator
Isovaleraldehyde	ChEBI
2-Methylbutanal-4	HMDB
3-Methyl-1-butanal	HMDB
3-Methyl-butanal	HMDB
3-Methyl-butyraldehyde	HMDB
3-Methylbutan-1-al	HMDB
3-Methylbutanal	HMDB
Isoamylaldehyde	HMDB
Isopentanal	HMDB
Isovaleric aldehyde	HMDB
Methyl butanal	HMDB
iso-Valeraldehyde	HMDB

Chemical Formula

C₅H₁₀O

Average Molecular Weight

86.1323

Monoisotopic Molecular Weight

86.073164942

IUPAC Name

3-methylbutanal

Traditional Name

isovaleraldehyde

CAS Registry Number

590-86-3

SMILES

[H]C(=O)CC(C)C

InChI Identifier

InChI=1S/C5H10O/c1-5(2)3-4-6/h4-5H,3H2,1-2H3

InChI Key

YGHRJJRRZDOVPD-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-hydrogen aldehydes

Alternative Parents

Substituents

Alpha-hydrogen aldehyde
Organic oxide
Hydrocarbon derivative
Short-chain aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

methylbutanal (CHEBI:16638 )
a small molecule (CPD-7031 )

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-51 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	14 mg/mL at 20 °C	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.29	ALOGPS
logP	1.05	ChemAxon
logS	-0.71	ALOGPS
pKa (Strongest Acidic)	18.56	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	25.49 m³·mol⁻¹	ChemAxon
Polarizability	10.12 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-3a38c8f6150bf1f43e74	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-5a3fd4f38dc36ebe58a1	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-3a38c8f6150bf1f43e74	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-5a3fd4f38dc36ebe58a1	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-4b322dc8237378d93057	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9000000000-7f4ac528265c8b3bf3ab	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9000000000-6e4f25dc68765a0e52ca	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9000000000-809684cd2152204e911f	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-0006-9000000000-3a38c8f6150bf1f43e74	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-0006-9000000000-5a3fd4f38dc36ebe58a1	2012-08-31	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-a8ed71d6e7d567b598b4	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kp-9000000000-043451832d2f37b1c7e1	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-3c57d920ca714b174bb3	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-030536579800c9e49940	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-be1f1229d7e13994d150	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-13768c049fd8e5c23464	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-a8ed71d6e7d567b598b4	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kp-9000000000-043451832d2f37b1c7e1	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-3c57d920ca714b174bb3	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-030536579800c9e49940	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-be1f1229d7e13994d150	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-13768c049fd8e5c23464	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-2091e44a102d8284a813	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-199420ebca1b5eda6369	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-0f801351f709d0e5abf6	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-fead34b12404197f107d	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-cf72963a4f1f9f7f2df0	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-cd0a0aa8e74bbc2b6344	2021-09-25	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-881fcc89b0f579b40793	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Not Available	2015-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2015-03-12	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	0.101 +/- 0.112 uM	PMID: 12463694	details
Detected and Quantified	0.174 +/- 0.203 uM	PMID: 12463694	details
Detected and Quantified	1 +/- 0.713 uM	PMID: 12463694	details
Detected and Quantified	0.42 +/- 0.64 mg/100g dry matter content	Brigitta Gaspardo...	details
Detected and Quantified	0.07 +/- 0.08 mg/100g dry matter content	Brigitta Gaspardo...	details

External Links

HMDB ID

HMDB0006478

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Isovaleraldehyde

METLIN ID

Not Available

PubChem Compound

11552

PDB ID

Not Available

ChEBI ID

16638

References

Synthesis Reference

Roelen, O. Synthesis of aldehydes and derivatives from olefins, carbon monoxide, and hydrogen. Angew. Chem. (1948), A60 62. CAN 44:46679 AN 1950:46679

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Toso B, Procida G, Stefanon B: Determination of volatile compounds in cows' milk using headspace GC-MS. J Dairy Res. 2002 Nov;69(4):569-77. [PubMed:12463694 ]
Brigitta Gaspardo, Giuseppe Procida, Saša Volarič, Sandy Sgorlon & Bruno Stefanon (2009). Brigitta Gaspardo et al. Determination of volatile fractions in raw milk and ripened cheese by means of GC-MS. Results of a survey performed in the marginal area between Italy and Slovenia. Italian Jounal of Animal Science Vol 8, 377-390, 2009. Italian Journal of Animal Science .

Showing metabocard for Iso-Valeraldehyde (BMDB0006478)

Structure for BMDB0006478 (Iso-Valeraldehyde)