CAS 19317-11-4 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienal (HCID 5280598)

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Basic information

CAS: 19317-11-4
Standard SMILES: CC(C)=CCC/C(C)=C/CC/C(C)=C/C=O
InChIKey: YHRUHBBTQZKMEX-YFVJMOTDSA-N
Molecular formula: C15H24O
Average molar mass: 220.35 g/mol
Monoisotopic mass: 220.18271539

Overview

Farnesal is a farnesane sesquiterpenoid and an enal.

Names & identifiers

Preferred name: (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienal
IUPAC: (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienal
English name: FARNESAL
Molecular formula: C15H24O
Molecular weight: 220.35

Names & synonyms

502-67-0(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienal(2E,6E)-FarnesalE,E-Farnesaltrans,trans-Farnesal2-trans,6-trans-Farnesaltrans-farnesal(E,E)-3,7,11-Trimethyl-2,6,10-dodecatrienaltrans,trans-2,6-FarnesalFarnesal, (2E,6E)-(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrienal(2-trans,6-trans)-farnesal

Show more names

2,6,10-Dodecatrienal, 3,7,11-trimethyl-FARNESALFARNESONEAi3-32959FARNESAL 95%Farnesal, Pract.Einecs 242-957-9TIMTEC-BB SBB0077162,6,10-Farnesatrien-1-alFarnesal (mixed isomers)

2,6,10-Dodecatrienal, 3,7,11-trimethyl-, (E,E)-MFCD00038089G4E58106EW2,6,10-Dodecatrienal, 3,7,11-trimethyl-, (2E,6E)-(2-trans,6-trans)-3,7,11-trimethyldodeca-2,6,10-trienal3,7,11-Trimethyl-dodeca-2,6,10-trienalFarnesal (Mixture of Isomers, Technical Grade)(e,e)-farnesal

Database identifiers

Properties

Computed structural properties

XLogP: 4.9
Topological polar surface area: 17.1 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 1
Rotatable bonds: 7
Heavy atoms: 16
Formal charge: 0
Complexity: 289

Experimental & physicochemical properties

LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C15 isoprenoids (sesquiterpenes) [PR0103]

SpringerMaterials PropertiesOptical coefficient

Collision Cross Section146.91 Å² [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Boiling point: 126 · 126-129 °C3.5 mm Hg(lit.)
Density: 0.909 g/mL · 0.909 g/mL at 25 °C(lit.)
FLAVIS Number: 5.148 · 05.148 | Farnesal
refractive index: 20 · n20/D >1.4920(lit.)
FEMA: 4019 · 4019 | 3,7,11-TRIMETHYL-2,6,10-DODECATRIENAL
Flash point: 230 °F · >230 °F
storage temp.: Amber Vial, Refrigerator
solubility: Chloroform (Sparingly), Methanol (Sparingly)

Safety & regulation

Hazard information

Regulatory InformationChemical: 2,6,10-Dodecatrienal, 3,7,11-trimethyl-, (E,E)-

Safety data

F: 1-10
PPE: Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 2
tsca: TSCA listed
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
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Pharmacology

Cellular LocationsMembrane

Uses & manufacturing

General Manufacturing Information2,6,10-Dodecatrienal, 3,7,11-trimethyl-, (2E,6E)-: ACTIVE

Applications · 4 items

OccurrenceReportedly present in tomato, ginger and cardamom.

UsesFarnesone is s useful building block for organic synthesis

UsesFarnesal was used in the synthesis of sesquiterpene nanaimoal.

General DescriptionFarnesal has been reported as specific lipid substrate for aldo-keto reductase 1B10 (AKR1B10). The incubation of farnesol with the protoplast of Botryococcus braunii B race strain leads to the formation of farnesal and 3-hydroxy-2,3-dihydrofarnesal.