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2-Nonenal

HCID 5283335
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
18829-56-6
Standard SMILES
CCCCCC/C=C/C=O
InChIKey
BSAIUMLZVGUGKX-BQYQJAHWSA-N
Molecular formula
C9H16O
Average molar mass
140.22 g/mol
Monoisotopic mass
140.12011513

Overview

(E)-non-2-enal is a monounsaturated fatty aldehyde that is (2E)-non-2-ene which is carrying an oxo group at position 1. It has a role as a plant metabolite. It is a medium-chain fatty aldehyde, an enal and a monounsaturated fatty aldehyde.

Names & identifiers

Preferred name
2-Nonenal
IUPAC
(E)-non-2-enal
English name
TRANS-2-NONENAL
Molecular formula
C9H16O
Molecular weight
140.22

Names & synonyms

2-NONENAL2463-53-83-Hexylacroleinbeta-Hexylacrolein3-Hexyl-2-propenalHeptylideneacetaldehydealpha-Nonenyl aldehyde2-Nonen-1-al3-hexyl-acrolein2(E)-nonenal93C6BZW2TVDTXSID3047219
Show more names
FCC(2E)-2-NonenalTRANS-2-NONEN-1-ALNON-2-ENALFEMA 3213trans-2-Nonenal 97%2E-9CHOT2 NONENAL
RefChem:910150DTXCID1027219(2Z)-non-2-enaltrans-2-Nonenal18829-56-6(E)-Non-2-enal(E)-2-Nonenal2-Nonenal, (2E)-

Database identifiers

CAS
18829-56-6、2463-53-8
PubChem CID
5283335
DTXSID
DTXSID0047086
ChEMBL
CHEMBL450072
ChEBI
CHEBI:142592
UNII
8VEO649985
EC Number
219-562-5、242-609-6
Nikkaji
J110.528K、J59.356G

Properties

Computed structural properties

XLogP
3.1
Topological polar surface area
17.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
6
Heavy atoms
10
Formal charge
0
Complexity
94.9

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Aldehydes
LipidsFatty Acyls [FA] -> Fatty aldehydes [FA06]
SpringerMaterials PropertiesBoiling point
Fragrances · 2 items

Fragrance Ingredient (2-Nonenal) -> IFRA transparency List

Fragrance Ingredient (trans-2-Nonenal) -> IFRA transparency List

LogP3.11
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density0.855-0.865
Flavoring Agents · 2 items

EU Flavoring substances

EU Flavoring substances

Solubility · 2 items

Soluble in most fixed oils; Insoluble in water

Soluble (in ethanol)

Boiling Point88-90 °C (12 mm Hg)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

Aggregated GHS information provided per 1550 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H315 (> 99.9%): Causes skin irritation [Warning Skin corrosion/irritation]

Hazard information

Regulatory Information · 6 items

Chemical: 2-Nonenal

Chemical: 2-Nonenal, (E)-

Regulation (EC) No 1831/2003 (amended)

Regulation (EC) No 1831/2003 (amended)

2-Nonenal, (2E)-: Does not have an individual approval but may be used under an appropriate group standard

2-Nonenal: Does not have an individual approval but may be used under an appropriate group standard

Other Safety Information · 2 items

IMAP assessments - 2-Nonenal, (E)-: Environment tier I assessment

IMAP assessments - 2-Nonenal: Environment tier I assessment

Hazards SummaryA skin and strong eye irritant; [Alfa Aesar MSDS] See trans-2-Hexenal and 2-Dodecenal.
Hazard Classes and Categories · 2 items

Skin Irrit. 2 (> 99.9%)

Skin Irrit. 2 (100%)

Toxicology

TreatmentKidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.

Chemistry & industry

Pharmacology

Metabolism/MetabolitesUremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.

Uses & manufacturing

Uses · 2 items

Present in beer, coffee, cucumbers, watermelon, palm oil, potatoes, etc.; Used as a flavoring agent; [Merck Index]

Naturally produced by the body (endogenous).

Use Classification · 5 items

Fragrance Ingredients

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 2 items

2-Nonenal: ACTIVE

2-Nonenal, (2E)-: ACTIVE

Applications · 2 items

Usestrans-2-Nonenal is an unsaturated aldehyde that is a product of fatty acid peroxidation (and also has a grassy, cucumber smell). trans-2-Nonenal is naturally found in mushrooms, coffee and is also a constituent of carrot root. It also exhibits insecticidal effects.

General Descriptiontrans-2-Nonenal (T2N) is a volatile unsaturated aldehyde with an unpleasant greasy odor, present in low concentrations in barley, malt, and certain vegetables. It is utilized as an insect repellent, insecticide, and flavor compound. T2N is one of the basic components contributing to the off-flavor and odor in stored beer.

Upstream & downstream products

Upstream raw materials

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Related reactions

3 records
New reaction record
HRID 1657939 reaction equation
HRID 1657939As productuspto-grants-1976_06
HRID 1657942 reaction equation
HRID 1657942As productuspto-grants-1976_06
HRID 1657943 reaction equation
HRID 1657943As reactantuspto-grants-1976_06

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Refractive Index1.454-1.460
Physical Description · 2 items

Liquid; [Merck Index] Colorless liquid; [Alfa Aesar MSDS]

White to slightly yellow liquid; Powerful, penetrating fatty, violet aroma

Physicochemical properties

Melting point
-28 °C · -28°C (estimate)
Boiling point
88 · 88-90 °C12 mm Hg(lit.)
Density
0.846 g/mL · 0.846 g/mL at 25 °C(lit.)
vapor density
1 · >1 (vs air)
refractive index
20 · n20/D 1.453(lit.)
FEMA
3213 · 3213 | 2-NONENAL
FLAVIS Number
5.072 · 05.072 | trans-2-Nonenal
Flash point
184 °F · 184 °F
storage temp.
Refrigerator (+4°C)
solubility
Chloroform (Slightly), Methanol (Slightly)
form
Liquid
color
Clear colorless to pale yellow
Odor
1 % · at 1.00 % in dipropylene glycol. fatty green cucumber aldehydic citrus
Odor Type
fatty
biological source
synthetic
Water Solubility
Soluble in Alcohol , and oils. Insoluble in water.
Sensitive
Air Sensitive
Merck
14 · 14,6676
JECFA Number
1362 · 1362
Henry's Law Constant
5.8 · 5.8×10-2 mol/(m3Pa) at 25℃, Roberts and Pollien (1997)
Major Application
cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care
Cosmetics Ingredients Functions
PERFUMING
InChI
1S/C9H16O/c1-2-3-4-5-6-7-8-9-10/h7-9H,2-6H2,1H3/b8-7+
InChIKey
BSAIUMLZVGUGKX-BQYQJAHWSA-N
SMILES
[H]C(=O)C(\[H])=C(/[H])CCCCCC
LogP
3.17 · 3.17
CAS DataBase Reference
18829 · 18829-56-6(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
8 VEO649985 · 8VEO649985
EPA Substance Registry System
2 · 2-Nonenal, (2E)- (18829-56-6)
UNSPSC Code
85151701 · 85151701
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
261 · P261-P305+P351+P338
Hazard Codes
Xi
Risk Statements
36 · 36/37/38
Safety Statements
26 · 26-36/37/39
RIDADR
1993 · NA 1993 / PGIII
WGK Germany
3 · 3
RTECS
8509050 · RA8509050
TSCA
TSCA listed
HazardClass
3 · 3
PackingGroup
II
HS Code
29121900 · 29121900
Storage Class
10 · 10 - Combustible liquids
Hazard Classifications
2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Health EffectsChronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Exposure RoutesEndogenous, Ingestion, Dermal (contact)
Toxicity Summary · 1 item

Uremic toxins such as 2-Nonenall are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869).

Signs and Symptoms · 1 item

As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

wgk
3
tsca
TSCA listed
rtecs
RA8509050
ridadr
NA 1993 / PGIII
hs_code
29121900
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
26-36/37/39
hazard_class
3
Storage Class
10 - Combustible liquids
packing_group
II
Hazard statements
H315-H319-H335
Hazard Classifications
Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements
P261-P305+P351+P338
2-Nonyn-1-al diethyl acetal1,1,3-Triethoxynonanetrans-2-Nonenetrans-2-Nonen-1-ol7-Tetradecenetrans-1-Iodo-1-octene1-Octyne1-Bromohexane
Additional notes · 1 item

DefinitionChEBI: (E)-non-2-enal is a monounsaturated fatty aldehyde that is (2E)-non-2-ene which is carrying an oxo group at position 1. It has a role as a plant metabolite. It is a monounsaturated fatty aldehyde, an enal and a medium-chain fatty aldehyde.