Showing Compound Geranial (FDB013702)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:51 UTC

Update date

2019-11-26 03:08:53 UTC

Primary ID

FDB013702

Secondary Accession Numbers

FDB013721

Chemical Information

FooDB Name

Geranial

Description

Geranial, also known as (2E)-geranial or alpha-citral, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Thus, geranial is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on Geranial.

CAS Number

141-27-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2E)-Geranial	ChEBI
(e)-Citral	ChEBI
(e)-Geranial	ChEBI
alpha-Citral	ChEBI
Citral a	ChEBI
Lemonal	ChEBI
trans-Citral	ChEBI
a-Citral	Generator
Α-citral	Generator
(2E)-3,7-Dimethyl-2,6-octadienal	HMDB
(e)-3,7-Dimethyl-2,6-octadienal	HMDB
(e)-3,7-Dimethylocta-2,6-dienal	HMDB
3,7-Dimethyl-(2E)-2,6-octadienal	HMDB
3,7-Dimethyl-(e)-2,6-octadienal	HMDB
3,7-Dimethyl-trans-2,6-octadienal	HMDB
alpha -Citral	HMDB
beta-Geranial	HMDB
Citral-a	HMDB
Genanial	HMDB
Geranal	HMDB
trans-3,7-Dimethyl-2,6-octadienal	HMDB
(Z)-Citral	MeSH, HMDB
Citral	MeSH, HMDB
(2E)-3,7-Dimethyl-2,6-octadien-1-al	HMDB
(E)-3,7-Dimethyl-2,6-octadienal	HMDB
(E)-Neral	HMDB
Geranaldehyde	HMDB
Geranial	HMDB
beta-Neral	HMDB
trans-3,7-Dimethyl-2,6-octadien-1-al	HMDB
trans-Geranial	HMDB
β-Geranial	HMDB
β-Neral	HMDB
3,7-Dimethyl-2,6-octadien-1-al	HMDB
3,7-Dimethyl-2,6-octadienal	HMDB
(2E)-3,7-Dimethylocta-2,6-dienal	biospider
(E)-3,7-Dimethylocta-2,6-dienal	biospider
(E)-Citral	biospider
(E)-Geranial	biospider
α-Citral	biospider
2,6-Octadienal, 3,7-dimethyl-, (2E)-	biospider
2,6-Octadienal, 3,7-dimethyl-, (E)-	biospider
α-citral	Generator

Predicted Properties

Property	Value	Source
Water Solubility	0.4 g/L	ALOGPS
logP	3.37	ALOGPS
logP	2.66	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	-4.1	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	4	ChemAxon
Refractivity	50.12 m³·mol⁻¹	ChemAxon
Polarizability	18.6 Å³	ChemAxon
Number of Rings	0	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

C10H16O

IUPAC name

(2E)-3,7-dimethylocta-2,6-dienal

InChI Identifier

InChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7+

InChI Key

WTEVQBCEXWBHNA-JXMROGBWSA-N

Isomeric SMILES

CC(C)=CCC\C(C)=C\C=O

Average Molecular Weight

152.237

Monoisotopic Molecular Weight

152.120115135

Classification

Description

Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Acyclic monoterpenoids

Alternative Parents

Substituents

Acyclic monoterpenoid
Medium-chain aldehyde
Enal
Alpha,beta-unsaturated aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

enal (CHEBI:16980 )
monoterpenoid (CHEBI:16980 )
Acyclic monoterpenoids (C01499 )
Linear monoterpenes (C01499 )
Acyclic monoterpenoids (LMPR0102010003 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Cell and elements:

Extracellular

Subcellular:

Biofluid and excreta:

Saliva

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Household products:

Antimicrobial agent

Food and nutrition:

Flavoring agent

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 78.90%; H 10.59%; O 10.51%	DFC
Melting Point	Not Available
Boiling Point	Bp20 119°	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	Not Available
Refractive Index	n20D 1.4898	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-014l-9100000000-92c761fd6ee64c67e40e	2014-09-20	View Spectrum
GC-MS	Geranial, non-derivatized, GC-MS Spectrum	splash10-014l-9000000000-ccb0a3f327b5d2362bb9	Spectrum
GC-MS	Geranial, non-derivatized, GC-MS Spectrum	splash10-014i-9100000000-131249cb1d7fb343fe10	Spectrum
GC-MS	Geranial, non-derivatized, GC-MS Spectrum	splash10-014i-9100000000-dcdfd8342f2d4ce5a439	Spectrum
GC-MS	Geranial, non-derivatized, GC-MS Spectrum	splash10-014i-9100000000-3c1a8e898f563c833b2c	Spectrum
GC-MS	Geranial, non-derivatized, GC-MS Spectrum	splash10-00kf-9000000000-90723459c49195367705	Spectrum
GC-MS	Geranial, non-derivatized, GC-MS Spectrum	splash10-014l-9000000000-ccb0a3f327b5d2362bb9	Spectrum
GC-MS	Geranial, non-derivatized, GC-MS Spectrum	splash10-014i-9100000000-131249cb1d7fb343fe10	Spectrum
GC-MS	Geranial, non-derivatized, GC-MS Spectrum	splash10-014i-9100000000-dcdfd8342f2d4ce5a439	Spectrum
GC-MS	Geranial, non-derivatized, GC-MS Spectrum	splash10-014i-9100000000-3c1a8e898f563c833b2c	Spectrum
GC-MS	Geranial, non-derivatized, GC-MS Spectrum	splash10-00kf-9000000000-90723459c49195367705	Spectrum
GC-MS	Geranial, non-derivatized, GC-MS Spectrum	splash10-014l-9000000000-ccb0a3f327b5d2362bb9	Spectrum
GC-MS	Geranial, non-derivatized, GC-MS Spectrum	splash10-014i-9100000000-131249cb1d7fb343fe10	Spectrum
GC-MS	Geranial, non-derivatized, GC-MS Spectrum	splash10-014i-9100000000-dcdfd8342f2d4ce5a439	Spectrum
GC-MS	Geranial, non-derivatized, GC-MS Spectrum	splash10-014i-9100000000-3c1a8e898f563c833b2c	Spectrum
GC-MS	Geranial, non-derivatized, GC-MS Spectrum	splash10-00kf-9000000000-90723459c49195367705	Spectrum
GC-MS	Geranial, non-derivatized, GC-MS Spectrum	splash10-014l-9000000000-ccb0a3f327b5d2362bb9	Spectrum
GC-MS	Geranial, non-derivatized, GC-MS Spectrum	splash10-014i-9100000000-131249cb1d7fb343fe10	Spectrum
GC-MS	Geranial, non-derivatized, GC-MS Spectrum	splash10-014i-9100000000-dcdfd8342f2d4ce5a439	Spectrum
GC-MS	Geranial, non-derivatized, GC-MS Spectrum	splash10-014i-9100000000-3c1a8e898f563c833b2c	Spectrum
GC-MS	Geranial, non-derivatized, GC-MS Spectrum	splash10-00kf-9000000000-90723459c49195367705	Spectrum
Predicted GC-MS	Geranial, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0159-9300000000-625c688e32f3edaf287c	Spectrum
Predicted GC-MS	Geranial, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1900000000-84bd30b4e03200f6db52	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-1010-8900000000-8aa62bcc7a1bcaa41a1e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-9000000000-79a3e6745a117da8309b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-21d238fd55ee29af690f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1900000000-b84583833bad67467cf0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9700000000-a5e231c57e7f56a65d6d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0pb9-0900000000-70e7a03f5a911f54f098	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-3128155f72d867d46318	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9100000000-9b92fab117afca4b3a0a	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05o0-9100000000-9c5fcd575fed478bccf6	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05qc-9000000000-85ae79bf95f3094e7a85	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-1a9a16cf8ea66689ce6a	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16980

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB35092

CRC / DFC (Dictionary of Food Compounds) ID

JGH37-H:JGB05-S

EAFUS ID

Not Available

Dr. Duke ID

CITRAL-A|CITRAL-ALPHA|GERANIAL|TRANS-CITRAL

BIGG ID

Not Available

KNApSAcK ID

C00003036

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

141-27-5

GoodScent ID

rw1041341

SuperScent ID

Not Available

Wikipedia ID

Geranial

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 aflatoxin	35222	An agent that neutralizes or removes aflatoxins, toxic compounds produced by mold, reducing the risk of liver damage and cancer. Therapeutically, it is used to prevent aflatoxin poisoning, commonly in food safety and liver protection applications, and may have potential in cancer prevention and treatment.	DUKE
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
Anti Epstein-Barr virus	22587	An agent that targets and neutralizes the Epstein-Barr virus, reducing its replication and associated diseases, such as infectious mononucleosis and certain types of cancer, with therapeutic applications in immunocompromised patients and key medical uses in preventing and treating EBV-related disorders.	DUKE
Antitumor	35610	An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.	DUKE
Anti-viral	22587	An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.	DUKE
Anti-yeast	33281	An agent that inhibits the growth of yeast, playing a role in preventing fungal infections. Therapeutically, it is used to treat conditions such as candidiasis and athlete's foot, and has applications in managing digestive issues and skin infections.	DUKE
Chemopreventive	35610	An agent that prevents or delays the development of cancer, reducing the risk of tumor formation and progression. It plays a biological role in inhibiting carcinogenesis, and has therapeutic applications in cancer prevention, with key medical uses including reducing the risk of colorectal, breast, and prostate cancers.	DUKE
Estrogenic		An agent that mimics the effects of estrogen, regulating female reproductive processes and development. Therapeutically, estrogenic agents are used in hormone replacement therapy, contraception, and treating menopausal symptoms, as well as certain cases of osteoporosis and infertility.	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
Glutathionigenic		An agent that stimulates glutathione synthesis, playing a crucial role in antioxidant defense and cellular detoxification. It has therapeutic applications in reducing oxidative stress and inflammation, with key medical uses in neuroprotection, cancer treatment, and liver disease management.	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
Spasmolytic		An agent that relieves spasms of smooth muscle, playing a biological role in relaxing muscle contractions. Therapeutically, it's used to treat conditions like menstrual cramps, intestinal colic, and respiratory issues. Key medical uses include managing irritable bowel syndrome, asthma, and other smooth muscle disorders.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
lemon	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 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
mint	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
citrus	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.