495-02-3

Basic information

• Product Name: AURAPTENE
• Synonyms: 7-GERANYLOXYCOUMARIN;AURAPTENE;aurapten;7-[[(3E)-3,7-Dimethyl-2,6-octadienyl]oxy]-2H-1-benzopyran-2-one;Aurapten【C19H22O3】;7-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-2H-1-benzopyran-2-one;Auraptene, 98%, from Citrus maxima (Burm.) Merr.
• CAS NO: 495-02-3
• Molecular Formula: C₁₉H₂₂O₃
• Molecular Weight: 298.38
• Mol File: 495-02-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 91 °C
• Boiling Point: 455.5 °C at 760 mmHg
• Flash Point: 195.4 °C
• Appearance: white to off-white/
• Density: 1.079 g/cm³
• Vapor Pressure: 1.74E-08mmHg at 25°C
• Refractive Index: 1.548
• Storage Temp.: ?20°C
• Solubility: DMSO: >20mg/mL
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: AURAPTENE(CAS DataBase Reference)
• NIST Chemistry Reference: AURAPTENE(495-02-3)
• EPA Substance Registry System: AURAPTENE(495-02-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 495-02-3(Hazardous Substances Data)

Usage

Description

Auraptene, also known as 7-geranyloxy-6-methoxycoumarin, is a natural bioactive monoterpene coumarin ether found in various citrus fruits. It possesses therapeutic potential and has been shown to have remarkable effects in the prevention of degenerative diseases. Auraptene displays neuritogenic activity, neuroprotective effects, attenuates reactive oxygen species (ROS) production, and enhances mitochondrial respiration, which can mitigate Parkinson's disease-like behavior. Additionally, it exhibits hepatoprotective and chemopreventive activities.

Uses

Used in Pharmaceutical Industry:
Auraptene is used as a therapeutic agent for its neuroprotective properties, particularly in the treatment and prevention of neurodegenerative diseases such as Parkinson's disease. It is used for its ability to suppress inflammation and induce the production of glial cell line-derived neurotrophic factor (GDNF) and brain-derived neurotrophic factor (BDNF) in neuronal cells.
Used in Nutraceutical Industry:
Auraptene is used as a dietary supplement for its hepatoprotective and chemopreventive activities. It helps in the prevention of liver diseases and has the potential to prevent the development of cancer by inhibiting the growth of cancer cells.
Used in Cosmetic Industry:
Auraptene is used as an active ingredient in anti-aging and skin care products due to its antioxidant and anti-inflammatory properties. It helps in reducing the signs of aging, such as wrinkles and fine lines, and promotes healthy skin by protecting it from environmental stressors.

References

1) Bibak et al. (2019), A Review of the Pharmacological and Therapeutic Effects of Auraptene; Biofactors, 45 867 2) Furukawa et al. (2012), Neurotrophic Effects of Citrus Auraptene: Neuritogenic Activity in PC12 Cells; Int. J. Mol. Sci., 13 5338 3) Furukawa et al. (2020), Citrus Auraptene Induces Expression of Brain-Derived Neurotrophic Factor in Neuro2a Cells; Molecules, 25 1117 4) Jang et al. (2019), Auraptene Mitigates Parkinson’s Disease-Like Behavior by Protecting Inhibition of Mitochondrial Respiration and Scavenging Reactive Oxygen Species; Int. J. Mol. Sci., 20 3409 5) Wang et al. (2019), Hepatoprotection of Auraptene From the Peels of Citrus Fruits Against 17α-ethinylestradiol-induced Cholestasis in Mice by Activating Farnesoid X Receptor; Food Funct., 10 3839 6) Tanaka et al. (1998), Citrus Auraptene Exerts Dose-Dependent Chemopreventative Activity in Rat Large Bowel Tumorigenesis: The Inhibition Correlates With Suppression of Cell Proliferation and Lipid Peroxidation and With Induction of Phase II Drug-Metabolizing Enzymes; Cancer Res., 58 2550

InChI:InChI=1/C19H22O3/c1-14(2)5-4-6-15(3)11-12-21-17-9-7-16-8-10-19(20)22-18(16)13-17/h5,7-11,13H,4,6,12H2,1-3H3/b15-11+

Upstream product

• 142628-36-2 (R)-6-O-(4-geranyloxy-2-hydroxy)cinnamoylmarmin 
• 93-35-6 7-hydroxy-2H-chromen-2-one 
• 5389-87-7 1-chloro-3,7-dimethylocta-2,6-diene 

Downstream Products

• 5980-09-6 (6'R,2'E)-dihydroxy-6',7' dimethyl-3',7' octene-2' oxy-7 coumarine 
• 61347-54-4 (S)-7-(6,7-dihydroxy-3,7-dimethyloct-2E-enyloxy)chromen-2-one 
• 36413-96-4 7-(7-hydroxy-3,7-dimethyl-6-oxooct-2E-enyloxy)chromen-2-one 
• 130548-21-9 7-(6,7-dihydroxy-3,7-dimethyloct-2E-enyloxy)chromen-2-one 
• 108354-46-7 (8'-hydroxy-3',7'-dimethyl-2',6'-octadienyl)-7-oxy-cooumarin 
• 21499-17-2 Epoxyaurapten 
• 160238-94-8 (E)-3-[4-((E)-3,7-Dimethyl-octa-2,6-dienyloxy)-2-hydroxy-phenyl]-acrylic acid methyl ester 
• 36413-91-9 geiparvarin 
• 98066-12-7 (+/-)-(E)-7-<<(3-tetrahydro-5,5-dimethyl-4-oxo-2-furanyl)-2-butenyl>-oxy>-2H-1-benzopyran-2-one 
• 115028-73-4 (+)-(6'R,7'R,2'E)-epoxy-6',7' dimethyl-3',7' octene-2' tosyle-8' oxy-7 coumarine 
• 93-35-6 7-hydroxy-2H-chromen-2-one 

Relevant articles and documents

Identification and biological evaluation of grapefruit oil components as potential novel efflux pump modulators in methicillin-resistant Staphylococcus aureus bacterial strains

Grapefruit oil components were isolated and characterised and evaluated for intrinsic antibacterial activity and modulating effect in MRSA and MSSA strains. The grapefruit component 4-{[(E)-5-(3,3-dimethyl-2-oxiranyl)-3-methyl- 2-pentenyl]oxy}-7H-furo[3,2-g]chromen-7-one (2) enhanced the susceptibility of MRSA bacteria strains and other micro-organisms to agents, e.g. ethidium bromide and norfloxacin, to which these micro-organisms are normally resistant. Methicillin-resistant Staphylococcus aureus (MRSA) and MSSA strains were treated with: (a) grapefruit oil (GFO) components, isolated by chromatography and characterised by NMR and mass spectroscopy; (b) antimicrobial agents, or (c) a combination of both to evaluate (MIC determination) intrinsic antibacterial activity and to determine whether GFO components could modulate bacterial sensitivity to the anti-bacterial agents. Preliminary data suggested that the grapefruit component 4-{[(E)-5-(3,3-dimethyl-2-oxiranyl)-3-methyl-2-pentenyl] oxy}-7H-furo[3,2-g]chromen-7-one (2) enhances the susceptibility of test MRSA strains to agents, e.g., ethidium bromide and norfloxacin, to which these micro-organisms are normally resistant.