6-Octenal, 3,7-dimethyl-, (3R)- (HCID 75427)

Overview

(R)-(+)-citronellal is the (3R)-stereoisomer of 3,7-dimethyloct-6-enal (citronellal). It is an enantiomer of a (S)-(-)-citronellal.

Names & identifiers

Preferred name: 6-Octenal, 3,7-dimethyl-, (3R)-
IUPAC: (3R)-3,7-dimethyloct-6-enal
English name: (+)-CITRONELLAL
Molecular formula: C10H18O
Molecular weight: 154.25

Names & synonyms

(R)-3,7-Dimethyloct-6-enal6-Octenal, 3,7-dimethyl-, (3R)-6-Octenal, 3,7-dimethyl-, (R)-EINECS 219-194-5EC 219-194-56-Octenal, 3,7-dimethyl-, (theta)-RefChem:544134219-194-5(R)-(+)-Citronellal2385-77-5(+)-Citronellal(3R)-3,7-dimethyloct-6-enal

Show more names

D-CitronellalCITRONELLAL(D-)CITRONELLAL (R+)(+)-CITRONELLAL 95+%Citronellal Impurity 1(R)-(+)-Citronellal,90%

(R)-citronellal(3R)-(+)-citronellal(3R)-3,7-Dimethyl-6-octenal(R)-3,7-dimethyl-6-octenalMFCD00067089(+)-Citronellal (>90%)3,7-Dimethyl-6-octenal, (3R)-CS-0089462

Database identifiers

CAS: 2385-77-5
PubChem CID: 75427
DTXSID: DTXSID6044482
ChEMBL: CHEMBL1081721
ChEBI: CHEBI:299
EC Number: 219-194-5
Nikkaji: J43.580E

Properties

Computed structural properties

XLogP: 3
Topological polar surface area: 17.1 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 1
Rotatable bonds: 5
Heavy atoms: 11
Formal charge: 0
Complexity: 132

Experimental & physicochemical properties

LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]

LogP · 2 items

3.83

Boiling Point207.00 °C. @ 760.00 mm Hg

Melting Point< 25 °C

Physical DescriptionSolid

Physicochemical properties

Melting point: 25 °C · 25°C
Boiling point: 207 °C · 207 °C(lit.)
Density: 0.851 g/mL · 0.851 g/mL at 25 °C(lit.)
vapor pressure: 33.9 Pa · 33.9Pa at 25℃
refractive index: 20 · n20/D 1.448(lit.)
Flash point: 185 °F · 185 °F
storage temp.: 2 · 2-8°C
solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly)
form: Oil
color: Colourless
Odor: 100 % · at 100.00 %. fresh herbal citrus
Odor Type: herbal
Viscosity: 1.82 mm2/s · 1.82mm2/s
Water Solubility: 88 mg/L · 88mg/L
Merck: 2329 · 2329
BRN: 1720791 · 1720791
InChI: 1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3/t10-/m1/s1
InChIKey: NEHNMFOYXAPHSD-SNVBAGLBSA-N
SMILES: C[C@H](CC\C=C(\C)C)CC=O
LogP: 3.83 at · 3.83 at 25℃
CAS DataBase Reference: 2385 · 2385-77-5(CAS DataBase Reference)
EPA Substance Registry System: 6 · 6-Octenal, 3,7-dimethyl-, (3R)- (2385-77-5)
UNSPSC Code: 12352114 · 12352114
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs: Respiratory system
PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36
WGK Germany: 3 · 3
TSCA: TSCA listed
HS Code: 2912190090 · 2912190090
Storage Class: 10 · 10 - Combustible liquids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

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

P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 146 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: 6-Octenal, 3,7-dimethyl-, (R)-

Status: Active Update: 13-02-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/22664

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
tsca: TSCA listed
hs_code: 2912190090
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
Storage Class: 10 - Combustible liquids
target organs: Respiratory system
Hazard statements: H315-H319-H335
REACH Registrations: Active
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Pharmacology

Cellular LocationsExtracellular

Uses & manufacturing

General Manufacturing Information6-Octenal, 3,7-dimethyl-, (3R)-: ACTIVE

Applications · 2 items

Usesinsect repellent

Uses(+)-Citronellal is a monoterpene compound that is formed by the metabolism of plants. (+)-Citronellal is a natural insect repellant, and is the main component of citronellal oil. (+)-Citronellal is also used as a starting material in the one pot synthesis of (-)-Menthol (M218875).