(3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one

• ChemBase ID: 104195
• Molecular Formular: C13H20O
• Molecular Mass: 192.2973
• Monoisotopic Mass: 192.15141526
• SMILES: CC(=O)/C=C/C1=C(C)CCCC1(C)C
• Canonical SMILES: CC(=O)/C=C/C1=C(C)CCCC1(C)C
• InChI: InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h7-8H,5-6,9H2,1-4H3
• InChIKey: PSQYTAPXSHCGMF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one; 4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one
• IUPAC Traditional name: β-ionone; 4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one
• Synonyms: beta-Ionone; 4-(2,6,6-Trimethyl-1-cyclohexenyl)-3-buten-2-one; β-Ionone; β-IRISONE; (E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one; (3E)-4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-3-buten-2-one; (E)-4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-3-buten-2-one; (E)-β-Ionone; Ionone beta; trans-β-Ionone; β-Ionone; beta-Ionone; 4-[2,6,6-Trimethyl-1-cyclohexen-1-yl]-3-buten-2-one; β-IONONE; 4-(2,6,6-三甲基-1-环己烯基)-3-丁烯-2-酮; β-紫罗兰酮; β-紫罗酮

Database IDs

• CAS Number: 79-77-6; 14901-07-6
• EC Number: 238-969-9; 201-224-3
• MDL Number: MFCD00001549
• Beilstein Number: 1909544
• Merck Index: 145056
• PubChem SID: 24901176; 24881042; 162092449; 24895924
• PubChem CID: 638014
• FEMA ID: 2595
• Council of Europe Number: 142
• Flavis Number: 7.008

CALCULATED PROPERTIES

• Acid pKa: 19.705359
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 3.2756236
• LogD (pH = 7.4): 3.2756236
• Log P: 3.2756236
• Molar Refractivity: 61.8221 cm^3
• Polarizability: 23.56227 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Clear Colorless to Pale Yellow Oil
• Melting Point: -49°C
• Boiling Point: 126-128 °C/12 mmHg(lit.); 126-128°C @ 12 mm; 126-128°C/12mm
• Flash Point: >113 °C; >235.4 °F; 112 °C; 112°C(233°F); 233.6 °F
• Density: 0.943; 0.945 g/mL at 25 °C(lit.); 0.95 g/ml
• Refractive Index: 1.5200; n20/D 1.52(lit.); n20/D 1.521
• Organoleptic: almond; balsam; berry; grape; jam; orange; floral; woody; fruity; peach; raspberry; rose; sweet; violet; vegetable; wine-like; minty

Safety Information

• Storage Condition: 2-8°C; Amber Vial, Refrigerator
• RTECS: EN0350000; EN0500000
• European Hazard Symbols: Nature polluting (N); Irritant (Xi)
• UN Number: 3082
• German water hazard class: 2
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 38-51/53; 51/53
• Safety Statements: 61
• TSCA Listed: 是
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H303; H315; H411
• GHS Precautionary statements: P273; P312
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3082 9/PG 3
• Storage Temperature: 2-8°C
• Regulation Compliance: EU Regulation 1334/2008 & 178/2002; FCC; FDA 21 CFR (172.515)

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥85%; ≥95.0% (GC); ≥97%; 96%
• Grade: FG; Kosher; natural (US); NI; purum
• Empirical Formula (Hill Notation): C13H20O
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

MP Biomedicals - 05211059

MP Biomedicals Rare Chemical collection

MP Biomedicals - 05214875

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02155072

(4-[2,6,6-Trimethyl-1-cyclohexen-1-yl]-3-buten-2-one) 1 ml = approx. 0.95 g

Sigma Aldrich - I12603

Packaging
100 g in glass bottle

Sigma Aldrich - W259500

Biochem/physiol Actions
Taste at 1-20 ppm
Other Notes
Natural occurrence: Tobacco, grape, grape brandy, orange juice, papaya, peach, raspberry, roasted almond, tea and spearmint.
Packaging
1 kg in glass bottle
1 sample in glass bottle
10, 20 kg in poly drum

Sigma Aldrich - W259525

Packaging
1 kg in glass bottle
1 sample in glass bottle
25, 100 g in glass bottle

Toronto Research Chemicals - I731280

An aroma compound commonly found in essential oils such as rose oil. It is an important fragrance chemical used in perfumery. β-Ionone is effective in the chemoprevention of rat mammary carcinogenesis.

REFERENCES

• Bondar, C. et al.: Cosm. Toil., 122, 73 (2007)
• Yu, S. et al.: J. Agric. Food Chem., 43, 2144 (2007)
• Zhou, R. et al.: Jing. Huag., 28, 253 (2007)