15116-13-9

Usage

Physical Properties

Colorless, odorless liquid; highly soluble in water; sweet taste

Uses

Commonly used in the production of sunless tanning products

Mechanism of Action

Reacts with amino acids in the skin to produce a temporary brown color, also known as a suntan

Safety

Considered safe for use in cosmetic products and has been approved for use by regulatory agencies such as the FDA

Sun Protection

Does not provide any protection from the sun's harmful UV rays; users should still use sunscreen when exposed to the sun.

Upstream product

• 638-29-9 n-valeryl chloride 
• 108-46-3 recorcinol 
• 2082-59-9 pentanoic anhydride 
• 109-52-4 valeric acid 

Downstream Products

• 372486-18-5 1-(2-hydroxy-4-methoxyphenyl)pentan-1-one 
• 85696-82-8 2-pentanyl-5-methoxyphenol 
• 15116-19-5 3-Methoxy-6-n-pentyl-1,4-benzoquinone 
• 128889-98-5 4-Butyl-7-hydroxy-3-phenyl-chromen-2-one 
• 97304-17-1 1-(2,4-dihydroxy-5-pentyl-phenyl)-ethanone 
• 533-24-4 4-pentyl resorcinol 
• 128889-93-0 Acetic acid 4-butyl-2-oxo-3-phenyl-2H-chromen-7-yl ester 
• 97304-13-7 2,4-dihydroxy-5-isopentenylvalerophenone 
• 97304-07-9 2,4-dihydroxy-3-isopentenylvalerophenone 

Relevant academic research and scientific papers

Determining Essential Requirements for Fluorophore Selection in Various Fluorescence Applications Taking Advantage of Diverse Structure-Fluorescence Information of Chromone Derivatives

Herein, we report our work exploring the essential requirements for fluorophore selection during the development of various fluorescence applications. We assembled a library of chromone-derived fluorophores with diverse structure-fluorescence properties, which allowed us to choose the fluorophore pairs with similar structures but differing fluorescence properties and compared the performance of the selected fluorophore pairs in three types of commonly used fluorescence applications. We found that the selection standard of a suitable fluorophore is variable depending on the application. (1) In fluorescence imaging, fluorophores with strong and constant fluorescence under various conditions, such as a large pH range, are preferred. Notably, (2) in the detection of bioactive species, fluorophores with relatively lower fluorescence quantum yield favor the detection sensitivity. Furthermore, (3) in enzymatic assays employing fluorescence, the key parameter is the binding affinity between the fluorophore and the enzyme.

Exploring efficacy of natural-derived acetylphenol scaffold inhibitors for α-glucosidase: Synthesis, in vitro and in vivo biochemical studies

The discovery of novel α-glucosidase inhibitors and anti-diabetic candidates from natural or natural-derived products represents an attractive therapeutic option. Here, a collection of acetylphenol analogues derived from paeonol and acetophenone were synthesized and evaluated for their α-glucosidase inhibitory activity. Most of derivatives, such as 9a–9e, 9i, 9m–9n and 11d–1e, (IC50 = 0.57 ± 0.01 μM to 8.45 ± 0.57 μM), exhibited higher inhibitory activity than the parent natural products and were by far more potent than the antidiabetic drug acarbose (IC50 = 57.01 ± 0.03 μM). Among these, 9e and 11d showed the most potent activity in a non-competitive manner. The binding processes between the two most potent compounds and α-glucosidase were spontaneous. Hydrophobic interactions were the main forces for the formation and stabilization of the enzyme - acetylphenol scaffold inhibitor complex, and induced the topography image changes and aggregation of α-glucosidase. In addition, everted intestinal sleeves in vitro and the maltose loading test in vivo further demonstrated the α-glucosidase inhibition of the two compounds, and our findings proved that they have significant postprandial hypoglycemic effects.

Synthesis and evaluation of aromatic methoxime derivatives against five postharvest phytopathogenic fungi of fruits. Main structure–activity relationships

The antifungal activity of a library of twenty-four aromatic methoximes was examined against five representative postharvest phytopathogenic fungi. The panel included Penicillium digitatum, Penicillium italicum, Rhizopus stolonifer, Botrytis cinerea and Monilinia fructicola, all of which cause relevant economic losses worldwide as a result of affecting harvested fruits. The minimum inhibitory concentrations and minimum fungicidal concentrations of each compound were defined and the main structure–activity relationships were determined. Although other congeners were more potent, drug likeliness considerations pointed to the methoxime derived from 2,4-dihydroxypropiophenone as the compound with the most suitable profile. The morphology of the colonies of the fungal strains treated with the methoxime was examined microscopically and the compound was also tested in freshly harvested peaches and oranges, exhibiting promising control profiles in both fruits, similar to those of the commercial agents Imazalil and Carbendazim.

Platinum complexes with anti-tumor activity and production method of platinum complexes with anti-tumor activity

The invention discloses platinum complexes with anti-tumor activity, and relates to the technical field of platinum complexes. The platinum complexes with anti-tumor activity comprise a complex A anda complex B, wherein with resorcinol as an initial raw m

Application of paeonol derivatives with vasodilator activity

The invention provides application of paeonol derivatives with vasodilator activity. The method comprises the following steps: carrying out a methylation reaction of 2,4-dihydroxyphenylpentanone underalkaline conditions, sequentially extracting and drying

Primulin derivative as well as synthesis method and application of primulin derivative

The invention discloses a primulin derivative with antibacterial activity shown as the structural general formula (I), wherein R is selected from C2-C20 alkyls. The primulin derivative is prepared from raw materials including m-dihydroxybenzene and a fatty acid derivative by the steps: carrying out Friedel-Crafts acylation and methylation to synthesize a paeonol derivative, and carrying out oxidization after carrying out carbonyl reduction. The primulin derivative has good antibacterial activity and can be used as a potential antibacterial agent.

Natural products as sources of new fungicides (II): antiphytopathogenic activity of 2,4-dihydroxyphenyl ethanone derivatives

A series of 17 simple 1-(2,4-dihydroxyphenyl) ethanones were synthesised, and their structures characterised by 1H, 13C NMR and ESI-MS. Their in vitro antifungal activities were evaluated against five phytopathogenic fungi including Glomerella cingulate, Botrytis cirerea, Fusarium graminearum, Curvularia lunata and Fusarium oxysporum f. sp. vasinfectum by the mycelial growth inhibition assay. Compounds 2g and 2h exhibited broad-spectrum inhibitory activity against the mycelial growth of the tested pathogens with IC50 values in the range of 16-36 g/mL, and in particular being more active to G. cingulate, with IC50 values of 16.50 and 19.25 g/mL, respectively, than the other pathogens. Preliminary SAR indicated that an α,β-unsaturated ketone unit of the alkyl chain of the compounds is the structure requirement for fungicidal action. The results suggested that 2g and 2h may be promising leads in the development of new antifungal agents.

Synthesis, antiproliferative, and c-Src kinase inhibitory activities of 4-oxo-4H-1-benzopyran derivatives

A new class of 4-oxo-4H-1-benzopyran derivatives were synthesized and their antiproliferative activity examined against a panel of three human cancer cell lines, that is, breast carcinoma (MDA-MB-468), ovarian adenocarcinoma (SK-OV-3), and colorectal adenocarcinoma (HT-29). Two compounds, that is, 3-hexyl-7,8-dihydroxy-4-oxo-4H-1-benzopyran and (E)-ethyl 3-(7-methoxy-4-oxo-4H-1-benzopyran-3-yl)acrylate were found to be potent against all three cancer cell lines studied at 50 μM concentration. Also, the inhibitory potency of the compounds was evaluated against active Src kinase. A few of these compounds exhibited modest Src kinase inhibitory activity (IC50 = 52-57 μM). Structure-activity relationship studies with respect to the nature and position of substituents on the lead compounds could be further exploited for the design and development of more potent antiproliferative agents and/or Src kinase inhibitors.

Arylalkyl ketones, benzophenones, desoxybenzoins and chalcones inhibit TNF-α induced expression of ICAM-1: Structure-activity analysis

The interaction between leukocytes and the vascular endothelial cells (EC) via cellular adhesion molecules plays an important role in the pathogenesis of various inflammatory and autoimmune diseases. Small molecules that block these interactions have been targeted as potential therapeutic agents against acute and chronic inflammatory diseases. In an effort to identify potent intercellular cell adhesion molecule-1 (ICAM-1) inhibitors, a large number of arylalkyl ketones, benzophenones, desoxybenzoins and chalcones and their analogs (54 in total) have been synthesized and screened for their ICAM-1 inhibitory activity. The structure-activity relationship studies of these compounds identified three potent chalcone derivatives and also demonstrated the possible mechanism for their ICAM-1 inhibitory activities. The most active compound was found to be 79. A large number of arylalkyl ketones, benzophenones, desoxybenzoins and chalcones as well as their analogs (54 in total) were synthesized and screened for their ICAM-1 inhibitory activity. The structure-activity relationship studies of these compounds identified three potent chalcone derivatives and also demonstrated a possible mechanism of their ICAM-1 inhibitory activities. The most active compound was found to be 79. Copyright

Synthesis and lipase-mediated stereoselective deacetylation of (±)-3-acetoxymethyl-3-alkyl-7-methoxychroman-4-ones

Six (±)-3-acetoxymethyl-3-alkyl-7-methoxychroman-4-ones have been synthesized in four steps starting with the coupling of resorcinol with corresponding aliphatic acid leading to the formation of 2,4-dihydroxyphenyl alkyl ketones, which upon monomethylation and hydroxymethylation, followed by acetylation afforded the racemic acetoxymethylated compounds in 17-30% overall yields. Candida rugosa lipase-catalyzed deacetylation of (±)-3-acetoxymethylchromanones in diisopropyl ether exhibited fairly moderate enantioselectivity.