IP Library › Granted Patent US 12,473,287
Granted Patent B2
US 12,473,287 · App. 18/400,142 · Granted Nov 18, 2025

Synthetic co-crystals of anhydrous guanine and process for preparing the same

Inventors: Dvir Gur (Rehovot, IL); Lia Addadi (Rehovot, IL); Stephen Weiner (Rehovot, IL)
Assignee: EcoCrystal Ltd.
C07D473/18C07B2200/13
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,473,287
App. No.
18/400,142
Granted
Nov 18, 2025
Kind
B2
Abstract

This invention is directed to synthetic co-crystals of anhydrous guanine and at least one additional material, wherein the co-crystals have a high refraction index and therefore, provide products with pearlescence or whiteness with high coverage. The invention is further directed to a process for the preparation of anhydrous guanine and of the co-crystals.

Claims (44)

1 . Synthetic co-crystals comprising anhydrous guanine and at least one additional material, wherein the synthetic co-crystals have a plate morphology, and wherein the at least one additional material is selected from the group consisting of hypoxanthine, xanthine, uric acid, isoguanine, theobromine, isoxanthopterin, xanthopterin, thymine, cytosine, uracil, guanosine, cytidine, thymidine, uridine, adenosine, and inosine.

2 . The synthetic co-crystals of claim 1 , wherein the at least one additional material is selected from the group consisting of hypoxanthine, xanthine and guanosine.

3 . The synthetic co-crystals of claim 1 comprising two or more additional materials.

4 . The synthetic co-crystals of claim 1 having a rectangular shape.

5 . The synthetic co-crystals of claim 1 , having a refractive index between 1.65 and 1.95.

6 . The synthetic co-crystals of claim 5 having a refractive index between 1.75 and 1.86.

7 . The synthetic co-crystals of claim 1 , which are 5-250 μm long.

8 . The synthetic co-crystals of claim 1 , which are 1-50 μm wide.

9 . The synthetic co-crystals of claim 1 , which are 20-500 nm thick.

10 . The synthetic co-crystals of claim 1 , which are 5-250 μm long, 1-50 μm wide, and 20-500 nm thick.

11 . The synthetic co-crystals of claim 1 having a smooth surface.

12 . The synthetic co-crystal of claim 1 comprising at least 50 mol % of guanine.

13 . The synthetic co-crystals of claim 1 comprising at least 0.01 mol % of the additional material.

14 . The synthetic co-crystals of claim 13 comprising 0.01-50 mol % of the additional material.

15 . The synthetic co-crystals of claim 1 , which are incorporated into a composition selected from the group consisting of paints, coatings, printing inks, plastics, cosmetic formulations, food products, paper, agricultural products, and medicaments.

16 . A process for preparing synthetic co-crystals of anhydrous guanine and at least one additional material according to claim 1 , wherein said process comprises the steps of:

(i) preparing a basic aqueous solution of guanine and the at least one additional material at a pH between about 11-14;

(ii) heating the basic aqueous solution to a temperature of between about 50-95° C.;

(iii) cooling the basic aqueous solution at a rate of between about 0.1-5.0 degrees/minute until reaching a temperature of about 4-20° C.;

(iv) adding an acid to the filtrate over a predefined period of time until a predetermined pH value is obtained, thereby providing a synthetic co-crystal suspension comprising co-crystals;

(v) allowing the synthetic co-crystal suspension to mature over a predetermined period of time; and

(vi) collecting the synthetic co-crystals from the crystal suspension.

17 . A process for preparing synthetic co-crystals of anhydrous guanine and at least one additional material according to claim 1 , wherein said process comprises the steps of:

(i) preparing a basic aqueous solution of guanine and the at least one additional material at a pH between about 11-14;

(ii) heating the basic aqueous solution to a temperature of between about 50-95° C.;

(iii) adding an acid to the basic aqueous solution over a predefined period of time until a predetermined pH value is obtained;

(iv) cooling the aqueous solution at a rate of between about 0.1-5.0 degrees/minute until reaching a temperature of about 4-20° C., thereby providing a synthetic co-crystal suspension comprising co-crystals;

(v) allowing the synthetic co-crystal suspension to mature over a predetermined period of time; and

(vi) collecting the synthetic co-crystals from the crystal suspension.

18 . A process for preparing synthetic co-crystals of anhydrous guanine and at least one additional material according to claim 1 , wherein said process comprises the steps of:

(i) preparing an acidic aqueous solution of guanine and the at least one additional material at a pH between about 0-3;

(ii) heating the acidic aqueous solution to a temperature of between about 50-95° C.;

(iii) cooling the acidic aqueous solution at a rate of between about 0.1-5.0 degrees/minute until reaching a temperature of about 4-20° C.;

(iv) adding a base to the filtrate over a predefined period of time until a predetermined pH value is obtained, thereby providing a synthetic co-crystal suspension comprising co-crystals;

(v) allowing the synthetic co-crystal suspension to mature over a predetermined period of time; and

(vi) collecting the synthetic co-crystals from the crystal suspension.

19 . A process for preparing synthetic co-crystals of anhydrous guanine and at least one additional material according to claim 1 , wherein said process comprises the steps of:

(i) preparing an acidic aqueous solution of guanine and the at least one additional material at a pH between about 0-3;

(ii) heating the acidic aqueous solution to a temperature of between about 50-95° C.;

(iii) adding a base to the acidic aqueous solution over a predefined period of time until a predetermined pH value is obtained;

(iv) cooling the aqueous solution at a rate of between about 0.1-5.0 degrees/minute until reaching a temperature of about 4-20° C., thereby providing a synthetic co-crystal suspension comprising co-crystals;

(v) allowing the synthetic co-crystal suspension to mature over a predetermined period of time; and

(vi) collecting the synthetic co-crystals from the crystal suspension.

20 . Synthetic co-crystals comprising anhydrous guanine and at least one additional material selected from the group consisting of hypoxanthine, xanthine, uric acid, isoguanine, theobromine, isoxanthopterin, xanthopterin, thymine, cytosine, uracil, guanosine, cytidine, thymidine, uridine, adenosine, and inosine; wherein (1) the guanine is present in an amount of at least 50 mol %; (2) the at least one additional material is present in an amount of at least 0.01 mol %, or (3) at least two of said additional materials are present.

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 5, 2024
From: GUR, DVIR
To: ECOCRYSTAL LTD.
Reel/Frame 066647/0227 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 5, 2024
From: GUR, DVIR; ADDADI, LIA; WEINER, STEPHEN
To: YEDA RESEARCH AND DEVELOPMENT CO. LTD.
Reel/Frame 066657/0270 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 5, 2024
From: YEDA RESEARCH AND DEVELOPMENT CO. LTD.
To: GUR, DVIR
Reel/Frame 066657/0426 →
Priority Claims (1)
IL 246428 · Jun 21, 2016 · national
Continuity (3)
Continuation 17504443 · Oct 18, 2021
Continuation 16311700
Related Publication 20240208977A1 · Jun 27, 2024
References Cited (34)
US 3557113A · Yamada et al. · 1971 [cited by applicant]
US 3692768A · Takata et al. · 1972 [cited by applicant]
US 3728329A · Yano et al. · 1973 [cited by applicant]
US 11149038B2 · Gur et al. · 2021 [cited by applicant]
US 11858936B2 · Gur · 2024 [cited by examiner]
US 20050142083A1 · Song et al. · 2005 [cited by applicant]
US 20060005742A1 · Moeschl et al. · 2006 [cited by applicant]
CN 111039943B · 2021 [cited by applicant]
DE 1930265A1 · 1969 [cited by applicant]
DE 102009044637A1 · 2011 [cited by applicant]
FR 2010977A1 · 1970 [cited by applicant]
WO 2004035692A1 · 2004 [cited by applicant]
WO 2014097134A1 · 2014 [cited by applicant]
Denton, “Review lecture: On the organization of reflecting surfaces in some marine animals,” Philosophical Transactions of The Royal Society of London, B. Biological Sciences 258(824): 285-313 (1970). [cited by applicant]
Hirsch et al., “Biologically Controlled Morphology and Twinning in Guanine Crystals,” Angewandte Chemie, International Edition 56(32): 9420-9424 (2017). [cited by applicant]
Kossell et al., “Über die Darstellung und quantitative Bestimmung des Arginins,” Hoppe-Seyler's Zeitschrift für Physiologische Chemie 135(1-4): 167-174 (1924). With machine translation. [cited by applicant]
Levy-Lior et al., “Biogenic Guanine Crystals from the Skin of Fish May Be Designed to Enhance Light Reflectance,” Crystal Growth & Design 8(2): 507-511 (2008). [cited by applicant]
Levy-Lior et al., “Guanine-Based biogenic photonic-crystal arrays in fish and spiders,” Advanced Functional Materials 20(2): 320-329 (2010). [cited by applicant]
Madden, “The unit cell of a mixed crystal of guanine and 8-azaguanine,” Acta Cryst. B29, 914-915 (1973). [cited by applicant]
Meisenheimer, “Die stickstoffhaltigen Bestandteile der Hefe. II. Mitteilung. Die Purinbasen und Diaminosäuren. Ergebnisse,” Hoppe-Seyler's Zeitschrift für Physiologische Chemie 114 (5-6): 205-249 (1921). With machine tr… [cited by applicant]
Mikulski et al., “Cobalt(II), copper(II) and zinc(II) chloride complexes involving both neutral and monoanionic guanine ligands,” Inorganica Chimica Acta, 108(4): L35-L37 (Dec. 1985). [cited by applicant]
Pfaff, “Natural Pearl Essence,” in: High Performance Pigments, Wiley-VCH, Weinheim (DE), Chapter 7.2.2.1, pp. 2, 103-104, 123. XP055775454 (2002). [cited by applicant]
Pfleiderer, “Purine, IV. über die Methylierung des 9-Methyl-guanins und die Struktur des Herbipolins,” Justus Liebigs Annalen der Chemie, 647(1): 167-173 (1961). With machine translation. [cited by applicant]
Thewalt et al., “The Crystal Structure of Guanine Monohydrate,” Acta Cryst. B27(12): 2358-2363 (1971). [cited by applicant]
Weiss et al., “Das komplexchemische Verhalten von Pyrimidinabkömmlingen, IV. Das komplexchemische Verhalten von Hydroxypurinen gegenüber Kupfer(II),” Hoppe-Seyler's Zeitschrift für Physiologische Chemie 340: 138-147 (19… [cited by applicant]
Zhe-Long Jin et al., “Constituents of Fish Scale Foil, a Natural Food Colorant,” Nihon Shokuhin Kagaku Gakkaishi—Japanese Journal of Food Chemistry, Nihon Shokuhin Kagaku Gakkai 12(2): 85-87, Abstract (2005). [cited by applicant]
Database Reaxys [Online]: Reed Elsevier Properties SA, XP002773266. Database accession No. 4930625 (Reaxys ID). [cited by applicant]
DE 102009044637, English language translation (2011). [cited by applicant]
Title 21—Food and Drugs; Chapter 1—Food and Drug Administration Department of Health and Human Services. Subchapter A—General; Part 73—Listing of Color Additives Exempt from Certification. Subpart B—Drugs; Sec. 73.1329 … [cited by applicant]
U.S. Appl. No. 17/504,443, Non-Final Rejection mailed Jan. 30, 2023. [cited by applicant]
U.S. Appl. No. 17/504,443, Notice of Allowance mailed Aug. 18, 2023. [cited by applicant]
U.S. Appl. No. 16/311,700, Requirement for Restriction mailed Jul. 14, 2020. [cited by applicant]
U.S. Appl. No. 16/311,700, Non-Final Rejection mailed Oct. 23, 2020. [cited by applicant]
U.S. Appl. No. 16/311,700, Notice of Allowance mailed Jun. 16, 2021. [cited by applicant]