Showing Compound Cuminaldehyde (FDB008724)

Record Information

Version

1.0

Creation date

2010-04-08 22:08:13 UTC

Update date

2020-09-17 15:35:00 UTC

Primary ID

FDB008724

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Cuminaldehyde

Description

Cuminaldehyde belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Cuminaldehyde, or 4-isopropylbenzaldehyde, is a natural organic compound with the molecular formula C10 H12O. It is a benzaldehyde with an isopropyl group in the 4-position. Cuminaldehyde is the biologically active constituent of Cuminum cyminum seed oil. Cuminaldehyde is a volatile compound representative of the cumin aroma. It has been detected to be present in trace amounts in the blood and milk of ewes fed with cumin seed (PMID: 8738023). In mammals, cuminaldehyde is metabolized by reduction but not by oxidation (PMID: 2815827). Cuminaldehyde is a constituent of the essential oils of eucalyptus, myrrh, cassia, and cumin, among others. It has a pleasant smell and contributes to the aroma of these oils. Cuminaldehyde can also be synthesized by the reduction of 4-isopropylbenzoyl chloride or by the formylation of cumene. It is used commercially in perfumes and other cosmetics.

CAS Number

122-03-2

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
4-Isopropylbenzaldehyde	ChEBI
Cumaldehyde	ChEBI
Cumic aldehyde	ChEBI
Cuminic aldehyde	ChEBI
Cuminyl aldehyde	ChEBI
p-Cumic aldehyde	ChEBI
p-Isopropylbenzaldehyde	ChEBI
p-Isopropylbenzenecarboxaldehyde	ChEBI
p-Isopropyl benzaldehyde	MeSH
4-(1-Methylethyl)benzaldehyde	HMDB
4-Isopropylbenzenecarboxylate	HMDB
Cuminal	HMDB
Cuminal P-(1-methylethyl)benzaldehyde	HMDB
P-Cuminic aldehyde	HMDB
P-Isopropyl-benzaldehyde	HMDB
4-(1-Methylethyl)benzaldehyde, 9CI	db_source
4-iPr-Benzaldehyde	biospider
4-Isopropyl benzaldehyde	biospider
Benzaldehyde, 4-(1-methylethyl)-	biospider
Benzaldehyde, p-isopropyl-	biospider
Cumal	biospider
Cuminal p-(1-methylethyl)benzaldehyde	biospider
Cuminaldehyde	db_source
FEMA 2341	db_source
p-(1-methylethyl)benzaldehyde	biospider
P-cumic aldehyde	biospider
P-cuminic aldehyde	biospider
P-isopropyl benzaldehyde	biospider
P-isopropyl-benzaldehyde	biospider
P-isopropylbenzaldehyde	biospider
P-isopropylbenzenecarboxaldehyde	biospider
p-Mentha-1,3,5-trien-1-al	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	2.73	ALOGPS
logP	2.93	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	-7.1	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	46.83 m³·mol⁻¹	ChemAxon
Polarizability	17.06 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H12O

IUPAC name

4-(propan-2-yl)benzaldehyde

InChI Identifier

InChI=1S/C10H12O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-8H,1-2H3

InChI Key

WTWBUQJHJGUZCY-UHFFFAOYSA-N

Isomeric SMILES

[H]C(=O)C1=CC=C(C=C1)C(C)C

Average Molecular Weight

148.205

Monoisotopic Molecular Weight

148.088815006

Classification

Description

Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

P-cymene
Aromatic monoterpenoid
Monocyclic monoterpenoid
Cumene
Phenylpropane
Benzaldehyde
Benzoyl
Aryl-aldehyde
Benzenoid
Monocyclic benzene moiety
Hydrocarbon derivative
Aldehyde
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

benzaldehydes (CHEBI:28671 )
Cyclic monoterpenes (C06577 )
a small molecule (CPD-1003 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Cell and elements:

Extracellular

Subcellular:

Biofluid and excreta:

Urine

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Industrial application:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 81.04%; H 8.16%; O 10.80%	DFC
Melting Point	Not Available
Boiling Point	Bp10 103-104°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d254 0.98	DFC
Refractive Index	n20D 1.5301	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0561-4900000000-eb2b3a37266bfb581bb3	2015-03-01	View Spectrum
GC-MS	Cuminaldehyde, non-derivatized, GC-MS Spectrum	splash10-0561-6900000000-5b0379bb7c7e6a17d117	Spectrum
GC-MS	Cuminaldehyde, non-derivatized, GC-MS Spectrum	splash10-0561-6900000000-5b0379bb7c7e6a17d117	Spectrum
Predicted GC-MS	Cuminaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-053r-3900000000-c02dbd8bf81f7768fc26	Spectrum
Predicted GC-MS	Cuminaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-0002-0900000000-dd3cd824f2abace2f474	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-0002-0900000000-3863618aab6990def399	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-0002-0900000000-3ebdf69e4e2457ce0b46	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0002-1900000000-22d80605ba571f6e3b96	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-056s-4900000000-a041347a1b6961438919	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-004i-9500000000-b789239b57425020f578	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-004i-9300000000-e621b7ac20c46d925927	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, positive	splash10-004i-9400000000-360e53edba5bc955bbf3	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-056r-9600000000-335c1d31bf11a5ce9c2c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, positive	splash10-056r-9600000000-7bb47d6aadc7432161d1	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 13V, positive	splash10-004i-9400000000-2f10fbe6182d457e96c7	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 15V, positive	splash10-0fb9-9100000000-2c7cf248afc0d63a8281	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-0a4i-3900000000-e7825163b5aabc234610	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 10V, positive	splash10-004i-9000000000-46d4cee1b5ac630ba9b8	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-7f1cf4b9bc08e5776672	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-1900000000-46a2d5a1f371a61f108e	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ldl-8900000000-60bce59455892fc6d3d9	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-36f6419f699e5430f11e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-9449fabcebe90dca9d03	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-4900000000-bbbb090a22b8e62ed75f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-2900000000-a82bc8469ac9379cd582	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-4900000000-9c19251b8683aebd8d31	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00mn-9300000000-df0d9626eb18c3efd162	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-c2f74e33d816bec66aa0	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-532ba12d245835d697bd	2021-09-24	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB02214

CRC / DFC (Dictionary of Food Compounds) ID

DTC96-Y:DTC96-Y

EAFUS ID

778

Dr. Duke ID

CUMINALDEHYDE

BIGG ID

Not Available

KNApSAcK ID

C00003039

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

GoodScent ID

SuperScent ID

Wikipedia ID

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Anti bacterial	33282	An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.	DUKE
Name	48318	flavor	DUKE
Fungicide	24127	An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.	DUKE
Irritant		An agent that causes slight inflammation or discomfort, stimulating a biological response. Therapeutically, it can be used to increase blood flow or stimulate healing. Key medical uses include treating wounds, skin conditions, and respiratory issues, such as congestion, by inducing a mild inflammatory response to promote recovery.	DUKE
Larvicide		An insecticide that targets the larval life stage of insects, preventing their development into adults. Its biological role is to control insect populations, and its therapeutic applications include managing mosquito-borne diseases such as malaria and dengue fever, as well as controlling pest infestations in agriculture and public health.	DUKE
Perfumery	48318	The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Sedative	35717	An agent that calms nervous activity, reducing anxiety and inducing relaxation. Its biological role is to slow down brain function, promoting sleep and relieving stress. Therapeutically, sedatives are used to manage insomnia, anxiety disorders, and seizures, as well as to prepare patients for medical procedures.	DUKE
Tyrosinase inhibitor	59997	An agent that blocks the activity of tyrosinase, an enzyme involved in melanin production, reducing skin pigmentation. Therapeutically used to treat hyperpigmentation disorders, such as melasma and vitiligo, and as a skin-lightening agent in dermatology.	DUKE
Ulcerogenic		An agent that causes the production of ulcers, often used to study gastrointestinal disease mechanisms. Its biological role involves disrupting mucosal defense, leading to ulcer formation. Therapeutically, understanding ulcerogenic agents informs the development of anti-ulcer medications. Key medical uses include researching gastric ulcer pathogenesis and testing potential treatments for ulcer prevention and healing.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
acid	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
sharp	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
oily	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
spicy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cumin	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
green	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.