Chromen-4-one derivatives for self-tanning and UV protection

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Solution Overview

Problem

Current self-tanning products do not provide adequate protection against UV radiation, as they lack UV-absorbing properties, leaving skin vulnerable to sunburn and long-term damage despite offering a temporary cosmetic tan.

Innovation Solution

Development of chromen-4-one derivatives that act as self-tanning agents, enhancing melanin synthesis and distribution, thereby providing both a tanning effect and improved protection against UV radiation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Illumination intensity

If traditional self-tanning substances (DHA, erythrulose) are used to achieve cosmetic tanning, then a temporary brownish skin color is obtained, but the skin lacks UV protection and remains vulnerable to sunburn and long-term damage

Engineering Contradiction:
Improveskin colorVSAvoidUV radiation damage
Core Design Contradiction:
Illumination intensityVSObject-affected harmful factors

Solution Approach 1:

The patent combines two previously separate functions into a single substance: self-tanning capability (producing brownish color) and UV protection. The chromen-4-one derivatives simultaneously react with skin proteins to produce cosmetic tanning while also absorbing UV radiation, eliminating the need for separate sunscreen application.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The chromen-4-one derivatives serve multiple functions at once: they act as self-tanning agents that produce color, UV filters that protect against radiation, and potentially antioxidants. This multi-functionality resolves the contradiction by making the tanning substance itself protective rather than vulnerable.

Inventive Principle:
Principle #6Universality (Multi-functionality)

2Reliability

If UV radiation is used to stimulate natural melanin production for skin protection, then melanin synthesis increases providing long-term protection, but acute skin damage (sunburn) and long-term damage (wrinkles, skin cancer) occur during the process

Engineering Contradiction:
Improveskin protectionVSAvoidacute and long-term skin damage
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The chromen-4-one derivatives are applied before UV exposure to establish protective mechanisms in advance. They either stimulate preemptive melanin production or provide immediate UV filtration, preparing the skin to withstand subsequent radiation without suffering acute damage like sunburn.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

Instead of allowing harmful UV radiation to directly damage skin cells, the invention converts the radiation energy into beneficial effects: the chromen-4-one derivatives absorb the harmful UV energy and either dissipate it harmlessly or use it to trigger protective melanin production, transforming the harmful radiation into a protective response.

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

3Reliability

If chromen-4-one derivatives are applied to accelerate melanin synthesis and distribution, then both tanning effect and UV protection are enhanced, but the complexity of the substance structure increases

Engineering Contradiction:
ImproveUV protection and tanning effectVSAvoidmolecular structure
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent systematically varies molecular parameters of chromen-4-one derivatives (substituents at different positions, chain lengths, functional groups) to optimize the balance between tanning effectiveness and UV protection. By adjusting these parameters, the invention achieves enhanced performance without unnecessarily complicating the core molecular structure.

Inventive Principle:
Principle #35Parameter changes

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The chromen-4-one derivatives accelerate and prolong the tanning reaction, offer natural-looking results, and enhance skin protection against UV damage, addressing the limitations of existing self-tanning products by promoting melanin synthesis and distribution while providing UV protection.

Implementation Method 1

Self-tanning agents can be reacted with the proteins and amino acids of the stratum corneum of the skin in the sense of a Maillard reaction

Methodology Applied
Scientific EffectMaillard reaction: Chemical Bonding

Implementation Method 2

Self-tanning agents can be reacted with the proteins and amino acids of the stratum corneum of the skin via a Michael addition

Methodology Applied
Scientific EffectMichael addition: Chemical Bonding

Implementation Method 3

UV light stimulates the production of melanin in these cells, which is transported into the kerantinocytes (homocytes) and becomes visible there as brown skin color

Methodology Applied
Scientific EffectMelanin synthesis enhancement: Enzyme

Implementation Method 4

Melanin protects the cell nuclei from further radiation and the negative effects it causes on the cell DNA

Methodology Applied
Scientific EffectUV absorption: Absorption (EM radiation)

Data Source

PatentEP2665717B17-acyloxy-chromen-4-one derivatives and their use as self-tanning substances
Publication Date: 2015.06.24 MERCK PATENT GMBH
  • EP2665717B1 patent drawing
  • EP2665717B1 patent drawing
  • EP2665717B1 patent drawing

AI summary

The invention relates to chromen-4-one derivatives of formula (I), to the use thereof as self-tanning substances or for increasing melanin synthesis, improving melanin transport and/or improving the distribution of melanin in suprabasal layers, and to preparations containing said chromen-4-one derivatives.