Basic information
- CAS
5146-66-7- Standard SMILES
CC(C)=CCCC(C)=CC#N- InChIKey
HLCSDJLATUNSSI-UHFFFAOYSA-N- Molecular formula
- C10H15N
- Average molar mass
- 149.23 g/mol
- Monoisotopic mass
- 149.12044948
Overview
citrus odourant
Names & identifiers
- Preferred name
- Geranyl nitrile
- IUPAC
- 3,7-dimethylocta-2,6-dienenitrile
- English name
- 3,7-Dimethyl-2,6-octadienenitrile
- Molecular formula
- C10H15N
- Molecular weight
- 149.23
Names & synonyms
citronitrileCitralva3,7-Dimethyl-2,6-octadienenitrile2,6-Octadienenitrile, 3,7-dimethyl-DTXSID3036286MS598KEL3MDTXCID1016286NSC-109052RefChem:922179225-918-03,7-Dimethylocta-2,6-dienenitrile5146-66-7
Show more names
LRT8GERANONITRILEGERANYLNITRIL3,7-dimethyl-6-octadienenitrile3,7-Dimethylocta-2,6-diennitrilGeranylNitrilecis-/trans-mixture
Geranyl nitrileGeranyl nitrile [mixture of (E)- and (Z)- isomers, (1:1)]SCHEMBL114125CHEMBL3185090HLCSDJLATUNSSI-UHFFFAOYSA-NAKOS028109913SY051492NS00003594
Database identifiers
- CAS
5146-66-7- PubChem CID
- 21768
- DTXSID
DTXSID3036286- ChEMBL
CHEMBL3185090- EC Number
- 225-918-0
Properties
Computed structural properties
- XLogP
- 3.3
- Topological polar surface area
- 23.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 3
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 208
Experimental & physicochemical properties
FragrancesFragrance substance (Geranyl nitrile) -> IFRA amendment 43
Physicochemical properties
- Boiling point
- 110 °C1.3 · 110 °C1.3 mm Hg(lit.)
- Density
- 0.853 g/mL · 0.853 g/mL at 25 °C(lit.)
- vapor pressure
- 3.7 · 3.7-4.82Pa at 20-25℃
- refractive index
- 20 · n20/D 1.475(lit.)
- Flash point
- 230 °F · >230 °F
- storage temp.
- Sealed in dry,Room Temperature
- form
- clear liquid
- Specific Gravity
- 0.866 · 0.866
- color
- A colourless or very pale yellow liquid.
- Odor
- 10 % · at 10.00 % in dipropylene glycol. citrus lemon nitrile aldehydic metallic
- Odor Type
- citrus
- Water Solubility
- SLIGHTLY SOLUBLE
- Henry's Law Constant
- 2.9 · 2.9×10-2 mol/(m3Pa) at 25℃, Helburn et al. (2008)
- LogP
- 2.7 · 2.7-3.47 at 35℃
- CAS DataBase Reference
- 5146 · 5146-66-7(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1-3
- FDA UNII
- 598 KEL3M · MS598KEL3M
- EPA Substance Registry System
- 2 · 2,6-Octadienenitrile, 3,7-dimethyl- (5146-66-7)
- Symbol(GHS)
- 6 · GHS06,GHS08,GHS09
- Signal word
- Danger
- Hazard statements
- 330 · H330-H341-H411
- Precautionary statements
- 260 · P260-P284-P310-P273-P281
- Hazard Codes
- Xn,N
- Risk Statements
- 51 · 51/53-68-20/21
- Safety Statements
- 36 · 36/37-61-23
- RIDADR
- 3082 · UN 3082 9/PG 3
- WGK Germany
- 1 · 1
- RTECS
- 5370000 · RG5370000
- TSCA
- TSCA listed
- HS Code
- 29269095 · 29269095
- Toxicity
- 50 value · The acute oral LD50 value in rats was reported as 31 g/kg and the acute dermal LD50 value in rabbits as 4.3 g/kg (Wohl. 1974).
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Danger
H340: May cause genetic defects [Danger Germ cell mutagenicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for 0.5% (2 of 364) of reports.
Danger
H340 (66.5%): May cause genetic defects [Danger Germ cell mutagenicity]
Hazard information
Regulatory Information
Chemical: 2,6-Octadienenitrile, 3,7-dimethyl-
Hazard Traits - Genotoxicity
Status: Active Update: 14-12-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/16500
Geranyl nitrile: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Geranyl and neryl nitriles: Human health tier II assessment
Hazard Classes and Categories
Muta. 1B (66.5%)
Germ cell mutagenicity - category 1B
Muta. 1B
Safety data
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- RG5370000
- ridadr
- UN 3082 9/PG 3
- hs_code
- 29269095
- Toxicity
- The acute oral LD50 value in rats was reported as 31 g/kg and the acute dermal LD50 value in rabbits as 4.3 g/kg (Wohl. 1974).
- risk_code
- 51/53-68-20/21
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08,GHS09
- hazard_code
- Xn,N
- safety_code
- 36/37-61-23
- Hazard statements
- H330-H341-H411
- REACH Registrations
- Active
- Precautionary statements
- P260-P284-P310-P273-P281
Chemistry & industry
Uses & manufacturing
IFRA Fragrance Standards
Geranyl nitrile
(2E)-3,7-dimethylocta-2,6-dienenitrile; 3,7-Dimethyl-2,6-octadienenitrile; Geranonitrile (isomer unspecified); 2,6-Octadienenitrile, 3,7-dimethyl-; Citranile (commercial name); Citralva (commercial name); Geranitrile (commercial name)
IFRA_STD_145.pdf
43
IFRA 51st Amendment - Guidance for the use of IFRA Standards
Prohibition: This material should not be used as a fragrance ingredient
Household ProductsCosmetics product ingredient: 3,7-dimethylocta-2,6- dienenitrile (Geranonitril)
General Manufacturing Information2,6-Octadienenitrile, 3,7-dimethyl-: ACTIVE
Applications
OccurrenceHas apparently not been reported to occur in nature.
UsesGeranyl Nitrite, is a substituted terpenoid odorant with a fruity odor quality. It is one of the most potent cyclase stimulators.
Preparation methods
PreparationFrom geranialoxime with acetic anhydride (Arctander. 1969).
Upstream & downstream products
Upstream raw materials
Suppliers59 total
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Related reactions
1 records
Compound notes
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