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W269905

Sigma-Aldrich

6-Methylcoumarin

≥99%, FCC, FG

Synonym(s):

6-methylchromen-2-one, Cocodescol, Pralina, Toncair, Toncarine

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About This Item

Empirical Formula (Hill Notation):
C10H8O2
CAS Number:
Molecular Weight:
160.17
FEMA Number:
2699
EC Number:
Council of Europe no.:
579
MDL number:
UNSPSC Code:
12164502
PubChem Substance ID:
Flavis number:
13.012
NACRES:
NA.21

biological source

synthetic

Quality Level

grade

FG
Halal
Kosher

Agency

meets purity specifications of JECFA

reg. compliance

EU Regulation 1334/2008 & 178/2002
FCC

Assay

≥99%

bp

303 °C/725 mmHg (lit.)

mp

73-76 °C (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

Organoleptic

coconut; creamy; sage; vanilla

SMILES string

Cc1ccc2OC(=O)C=Cc2c1

InChI

1S/C10H8O2/c1-7-2-4-9-8(6-7)3-5-10(11)12-9/h2-6H,1H3

InChI key

FXFYOPQLGGEACP-UHFFFAOYSA-N

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Application


  • Development of Sustainable Insecticide Candidates for Protecting Pollinators: Insight into the Bioactivities, Selective Mechanism of Action and QSAR of Natural Coumarin Derivatives against Aphids.: This study explores the potential of 6-Methylcoumarin and other natural coumarin derivatives as sustainable insecticides, highlighting their bioactivities and selective mechanism of action. The research aims to protect pollinators while targeting aphids, providing a promising alternative to conventional pesticides (Zhou et al., 2023).

  • Conductive Vial Electromembrane Extraction of Opioids from Oral Fluid.: This research presents a novel method using conductive vial electromembrane extraction for isolating opioids from oral fluid. While the primary focus is on opioids, the study utilizes 6-Methylcoumarin as a key component in the extraction process, showcasing its versatility in analytical chemistry applications (Skaalvik et al., 2023).

  • 6-Methylcoumarin Promotes Melanogenesis through the PKA/CREB, MAPK, AKT/PI3K, and GSK3β/β-Catenin Signaling Pathways.: This article investigates the role of 6-Methylcoumarin in promoting melanogenesis, detailing the molecular pathways involved. The findings suggest potential applications in dermatology and cosmetic science, particularly in skin pigmentation treatments (Kim et al., 2023).

  • Recursively Positive and Negative Chemotaxis Coupling with Reaction Kinetics in Self-Organized Inanimate Motion.: This research delves into the chemotactic behavior of inanimate particles, using 6-Methylcoumarin in the reaction kinetics studies. The study contributes to the understanding of self-organizing systems, with implications for material science and biophysics (Matsuo et al., 2023).

Biochem/physiol Actions

Taste at 5 ppm

Pictograms

Health hazardExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Resp. Sens. 1 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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E V Buehler et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 23(7), 689-694 (1985-07-01)
Guinea-pig tests were conducted on a known photocontact allergen, tetrachlorosalicylanilide (TCSA), a known phototoxin, 8-methoxypsoralen, two reportedly weak photoallergens, musk ambrette and 6-methylcoumarin, and a negative control, octylphenoxy polyethoxyethanol (Triton X-15). The data show that under the test conditions used
S Kato et al.
Toxicology and applied pharmacology, 81(2), 295-301 (1985-11-01)
6-Methylcoumarin (6-MC), a synthetic fragrance material, has been reported to be photoallergenic both in man and in guinea pigs. To elucidate the possible mechanism of photoallergenicity, 6-MC in ethanolic solution was exposed to 200 joules/cm2 of long-wavelength ultraviolet (UV) ranging
V A DeLeo et al.
Archives of dermatology, 128(11), 1513-1518 (1992-11-01)
Over a 6-year period, 187 patients with a history of photosensitivity were photopatch tested using standard techniques. Seventy-six patients were male and 111 were female. Most patients were white (151 patients). Two thirds of the patients were between the ages
H C Maguire et al.
The Journal of investigative dermatology, 79(3), 147-152 (1982-09-01)
We have induced photoallergic contact dermatitis in mice to 3,3',4',5 tetrachlorosalicylanilide (TCSA), chlorpromazine and 6-methylcoumarin. These compounds are known to produce photoallergic contact dermatitis in humans. The photoallergic contact dermatitis reaction in the mouse is immunologically specific viz. mice photosensitized
Barry C Pemberton et al.
Chemical communications (Cambridge, England), 46(2), 225-227 (2009-12-22)
Cucurbit[8]uril (as low as 10 mol%) acts as a supramolecular catalytic nanoreaction vessel and facilitates the photodimerization of coumarins in water leading to syn dimers. Saturation kinetics shows a sigmoidal dependence with a turnover number of 3.4 min(-1) and a

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