coumarin 151

Modify Date: 2024-01-02 23:41:45

coumarin 151 Structure
coumarin 151 structure
Common Name coumarin 151
CAS Number 53518-15-3 Molecular Weight 229.155
Density 1.5±0.1 g/cm3 Boiling Point 314.6±42.0 °C at 760 mmHg
Molecular Formula C10H6F3NO2 Melting Point 221-222 °C(lit.)
MSDS N/A Flash Point 144.1±27.9 °C

 Use of coumarin 151


7-Amino-4-(trifluoromethyl)coumarin (AFC, Coumarin 151) is a fluorescent marker for the sensitive detection of proteinases. The excitation and emission wavelengths are 400 and 490 nm, respectively.

 Names

Name coumarin 151
Synonym More Synonyms

 coumarin 151 Biological Activity

Description 7-Amino-4-(trifluoromethyl)coumarin (AFC, Coumarin 151) is a fluorescent marker for the sensitive detection of proteinases. The excitation and emission wavelengths are 400 and 490 nm, respectively.
Related Catalog
In Vitro Amino acid and peptide derivatives of 7-amino-4-(trifluoromethyl)coumarin are used to monitor peptidase activities. Caspase activation is measured using the fluorogenic compound N-acetyl-asp-glu-val-asp-7-Amino-4-(trifluoromethyl)coumarin (Ac-DEVD-AFC). This substrate rapidly enters cells where it is efficiently cleaved at the aspartate residue by specific caspases, yielding the fluorescent compound 7-Amino-4-(trifluoromethyl)coumarin (AFC). Following cell disruption, released 7-Amino-4-(trifluoromethyl)coumarin is separated on HPLC and detected by fluorescence. The appearance of 7-Amino-4-(trifluoromethyl)coumarin in cells is blocked by the pancaspase inhibitor benzyloxycarbonyl-val-ala-asp-fluoromethylketone, thus establishing that intracellular caspases are responsible for the cleavage[1]. γ-glutamyl-7-amino-4-(trifluoro-methyl)coumarin is synthesized and used as a substrate for fluirimetric assay of γ-gluta-myltranspeptidase. The reaction product 7-amino-4-(trifluoromethyl)coumarin is fluorescent at neutral pH values and with excitation and emission wavelengths of 400 and 490 nm, respectively, concentration is linearly related to fluorescence over the range of 10 to 300 pmol/3 mL reaction mixture[2].
References

[1]. Tao Z, et al. Caspase activation by anticancer drugs: the caspase storm. Mol Pharm. 2007 Jul-Aug;4(4):583-95.

[2]. White IN, et al. A continuous fluorometric assay for gamma-glutamyltranspeptidase. Anal Biochem. 1996 Jan 1;233(1):71-5.

 Chemical & Physical Properties

Density 1.5±0.1 g/cm3
Boiling Point 314.6±42.0 °C at 760 mmHg
Melting Point 221-222 °C(lit.)
Molecular Formula C10H6F3NO2
Molecular Weight 229.155
Flash Point 144.1±27.9 °C
Exact Mass 229.035065
PSA 56.23000
LogP 1.64
Vapour Pressure 0.0±0.7 mmHg at 25°C
Index of Refraction 1.562

 MSDS

Name: Coumarin 151 Laser Grade 99% (UV-Vis) Material Safety Data Sheet
Synonym: 2H-1-Benzopyran-2-One,7-Amino-4-(Trifluoromethyl)
CAS: 53518-15-3
Section 1 - Chemical Product MSDS Name:Coumarin 151 Laser Grade 99% (UV-Vis) Material Safety Data Sheet
Synonym:2H-1-Benzopyran-2-One,7-Amino-4-(Trifluoromethyl)

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS
CAS# Chemical Name content EINECS#
53518-15-3 2H-1-Benzopyran-2-One,7-Amino-4-(Trifl 99 258-599-1
Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
The toxicological properties of this substance have not been fully investigated.
Inhalation:
Harmful if inhaled. Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
Notes to Physician:
Treat symptomatically and supportively.

Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 53518-15-3: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: yellow
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 221 - 222 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C10H6F3NO2
Molecular Weight: 229.16

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Dust generation, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong acids, strong bases.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen fluoride gas, organic fluorides.
Hazardous Polymerization: Has not been reported

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 53518-15-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2H-1-Benzopyran-2-One,7-Amino-4-(Trifluoromethyl) - Not listed by ACGIH, IARC, or NTP.

Section 12 - ECOLOGICAL INFORMATION


Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 37/39 Wear suitable gloves and eye/face
protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 53518-15-3: No information available.
Canada
CAS# 53518-15-3 is listed on Canada's NDSL List.
CAS# 53518-15-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 53518-15-3 is listed on the TSCA inventory.


SECTION 16 - ADDITIONAL INFORMATION
N/A

 Safety Information

Hazard Codes Xn:Harmful;
Risk Phrases R20/21/22;R36/37/38
Safety Phrases S26-S36-S37/39
WGK Germany 3
HS Code 2932209090

 Synthetic Route

~46%

coumarin 151 Structure

coumarin 151

CAS#:53518-15-3

Literature: Kathuria, Abha; Priya, Nivedita; Chand, Karam; Singh, Prabhjot; Gupta, Anjali; Jalal, Sarah; Gupta, Shilpi; Raj, Hanumantharao G.; Sharma, Sunil K. Bioorganic and Medicinal Chemistry, 2012 , vol. 20, # 4 p. 1624 - 1638

~98%

coumarin 151 Structure

coumarin 151

CAS#:53518-15-3

Literature: Wang, Hongshe Monatshefte fur Chemie, 2013 , vol. 144, # 3 p. 411 - 414

~83%

coumarin 151 Structure

coumarin 151

CAS#:53518-15-3

Literature: Tetrahedron Letters, , vol. 43, # 50 p. 9195 - 9197

~%

coumarin 151 Structure

coumarin 151

CAS#:53518-15-3

Detail
Literature: Journal of Organic Chemistry, , vol. 45, # 12 p. 2283 - 2287

~%

coumarin 151 Structure

coumarin 151

CAS#:53518-15-3

Literature: Bioorganic and Medicinal Chemistry, , vol. 20, # 4 p. 1624 - 1638

~%

coumarin 151 Structure

coumarin 151

CAS#:53518-15-3

Literature: Bioorganic and Medicinal Chemistry, , vol. 20, # 4 p. 1624 - 1638

~%

coumarin 151 Structure

coumarin 151

CAS#:53518-15-3

Literature: Chemical Communications, , vol. 48, # 76 p. 9540 - 9542

~%

coumarin 151 Structure

coumarin 151

CAS#:53518-15-3

Literature: Chemical Communications, , vol. 48, # 76 p. 9540 - 9542

~%

coumarin 151 Structure

coumarin 151

CAS#:53518-15-3

Literature: ChemMedChem, , vol. 5, # 1 p. 103 - 117

 Customs

HS Code 2932209090
Summary 2932209090. other lactones. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

 Synonyms

7-Amino-4-(trifluoromethyl)-2H-chromen-2-one
2H-1-Benzopyran-2-one, 7-amino-4- (trifluoromethyl)-
7-amino-4-trifluoromethylchromen-2-one
MFCD00006858
Coumarin 151
7-NH2-4-CF3-coumarin
7-Amino-4-(trifluoromethyl)coumarin
7-amino-4-trifluoromethylcoumarin
7-amino-4-(trifluoromethyl)chromen-2-one
Coumarin 151,laser grade
EINECS 258-599-1
2H-1-Benzopyran-2-one, 7-amino-4-(trifluoromethyl)-
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