1,2,4-trimethoxy-5-[(1E)-prop-1-en-1-yl]benzene

• ChemBase ID: 104120
• Molecular Formular: C12H16O3
• Molecular Mass: 208.25364
• Monoisotopic Mass: 208.10994437
• SMILES: COc1c(OC)cc(/C=C/C)c(OC)c1
• Canonical SMILES: C/C=C/c1cc(OC)c(cc1OC)OC
• InChI: InChI=1S/C12H16O3/c1-5-6-9-7-11(14-3)12(15-4)8-10(9)13-2/h5-8H,1-4H3
• InChIKey: RKFAZBXYICVSKP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,2,4-trimethoxy-5-[(1E)-prop-1-en-1-yl]benzene; 1,2,4-trimethoxy-5-(prop-1-en-1-yl)benzene
• IUPAC Traditional name: 1,2,4-trimethoxy-5-[(1E)-prop-1-en-1-yl]benzene; asarone
• Synonyms: (E)-1,2,4-trimethoxy-5-(prop-1-en-1-yl)benzene; cis-1-Propenyl-2,4,5-trimethoxybenzene; β-Asarone; alpha-Asarone; trans-1,2,4-Trimethoxy-5-(1-propenyl)benzene; trans-1-Propenyl-2,4,5-trimethoxybenzene; α-Asarone; Alpha-asarone; 1,2,4-Trimethoxy-5-propenylbenzene; ASARONE; alpha-Azaron; cis-Isoelemicin; 2,4,5-Trimethoxyphenyl-2-propene; 顺式-2,4,5-三甲氧基-1-丙烯基苯; β-细辛醚; 反式-1-丙烯基-2,4,5-三甲氧基苯; 反式-1,2,4-三甲氧基-5-(1-丙烯基)苯; α-细辛醚

Database IDs

• CAS Number: 2883-98-9; 5273-86-9
• EC Number: 220-743-6; 226-096-6
• MDL Number: MFCD00064457; MFCD00009281
• Beilstein Number: 1910605; 1910606
• PubChem SID: 24853852; 24847008; 162092775
• PubChem CID: 636822
• CHEMBL: 333306
• Chemspider ID: 552532
• Wikipedia Title: Asarone

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.623569
• LogD (pH = 7.4): 2.623569
• Log P: 2.623569
• Molar Refractivity: 60.8074 cm^3
• Polarizability: 23.236055 Å^3
• Polar Surface Area: 27.69 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: insoluble in water
• Apperance: colorless solid substance
• Melting Point: 57-61 °C; 57-61 °C(lit.); 62-63 °C
• Boiling Point: 296 °C; 296 °C(lit.)
• Flash Point: 113 °C; 235.4 °F
• Density: 1.028 g/cm^-3; 1.073 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.558; n20/D 1.558(lit.)

Safety Information

• Storage Condition: 0°C, Protect from light
• RTECS: DC2975000; DC3000000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 22-24/25; 23-24/25
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Pharmacology Properties

• Mechanism of Action: Antihypercholesterolaemic,; CNS depressant agent

Product Information

• Purity: ~70% (GC); ≥97.0% (GC); 98%
• Grade: analytical standard, for terpene analysis; technical
• Biological Source: Constit. of Asarum spp.
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Anticonvulsant; Antihypercholesterolaemic and cholelytiasic agent
• Linear Formula: (CH3O)3C6H2CH=CHCH3

DETAILS

MP Biomedicals - 05210552

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02154798

(1,2,4-Trimethoxy-5-propenylbenzene) trans-Isomer

InterBioScreen - BB_NC-2561

Acorus tatarinowii Schott

Sigma Aldrich - 231282

Packaging
1, 5 g in glass bottle

REFERENCES

• Bjornstad K, Helander A, Hulten P, Beck O (2009). "Bioanalytical investigation of asarone in connection with Acorus calamus oil intoxications
• Asarone". The Merck Index. 14th edition. Merck Research Laboratories. 2006. pp. 135