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Innovative Highly Selective Chemical Synthesis Process for High-Functionality Cis-Xanthophylls (9-Cis / 9,9'-Di-Cis Astaxanthin)

Introduction & Joint Development of a Mild, Precise Synthesis for High-Purity Cis-Astaxanthin (5x Antioxidant Activity & 50x Solubility vs. Trans) and Its Applications.

Advantages

‐ Highly Selective Chemical Synthesis Under Mild Conditions: A novel synthetic method directly building target cis-isomers (9-cis / 9,9'-di-cis) with high purity without harsh thermal isomerization.
‐ Precise Ratio Control via Environmental Parameters: Process technology freely controlling yield ratios of 9-cis and rare 9,9'-di-cis isomers solely via light irradiation parameters.
- High-Efficiency Supply of Single Isomers: Superior productivity eliminating complex fractionation steps, overwhelming conventional thermal isomerization methods (total cis-ratio < 40%).
- Applications to High-Value Esters: Highly efficient direct synthetic application to AST-DHA possessing brain autophagy activation effects.

Current Stage and Key Data

Lab-scale synthesis and evaluation completed (Sample provision up to ~1g available under MTA).
‐ Highly Selective Process Validation: Achieved yields of 58% for 9-cis isomer under light irradiation and 40% for 9,9'-di-cis isomers under dark conditions.
- Validation of Peak Activity and Sustained Function: Demonstrated ~5x higher antioxidant capacity (singlet oxygen absorption capacity) for 9,9'-di-cis isomer vs. trans-form, maintaining sustained activity and color stability for 60 minutes at the same concentration.

Partnaring Model

Patent licensing of the manufacturing technology, joint development of scale-up and mass-production processes, and product application development (functional foods, cosmetics, feed, pharmaceuticals, etc.) utilizing compounds and compositions obtained through this technology.
- Partner Industry Candidates: Cosmetics & Skincare, Functional Foods, Supplements & Ingredients, Aquaculture, Feed & Food Tech, Pharmaceuticals

Background

While xanthophylls like astaxanthin are widely used antioxidant pigments, conventional commercial products are mostly all-trans isomers with poor solubility and low bioavailability (<1% absorption). Highly active "9-cis" and "9,9'-di-cis" isomers offer superior ROS scavenging power and bioavailability, but conventional thermal isomerization yields complex mixtures, driving reagent costs to ~200,000 JPY/mg. This world-first direct chemical synthesis technology overcomes these limits by constructing target cis-configurations with high purity under mild conditions, enabling cost-effective, bulk production of high-value cis-xanthophylls.
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Principal Investigator

Naoto Yamasaki (Graduate School of Pharmaceutical Science, Nagoya University, Tokai National Higher Education and Research System)

Patents and References

Patent pending (unpublished yet)

Project No:bk-05624