Laccaic acid

Last updated
Laccaic acid A
Laccaic Acid A.svg
Names
IUPAC name
7-[5-(2-acetamidoethyl)-2-hydroxyphenyl]-3,5,6,8-tetrahydroxy-9,10-dioxoanthracene-1,2-dicarboxylic acid
Other names
Red lac, Shellac, Lac dye
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
  • InChI=1S/C26H19NO12/c1-8(28)27-5-4-9-2-3-12(29)10(6-9)15-22(33)19-18(24(35)23(15)34)20(31)11-7-13(30)16(25(36)37)17(26(38)39)14(11)21(19)32/h2-3,6-7,29-30,33-35H,4-5H2,1H3,(H,27,28)(H,36,37)(H,38,39)
  • CC(=O)NCCC1=CC(=C(C=C1)O)C2=C(C3=C(C(=C2O)O)C(=O)C4=CC(=C(C(=C4C3=O)C(=O)O)C(=O)O)O)O
Properties
C26H19NO12
Molar mass 537.44 g·mol−1
Density 1.7±0.1 g.cm3
Vapor pressure 0.0±0.3 mmHg at 25°C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Laccaic acids or laccainic acids are a group of five anthraquinone derivatives, designated A through E, which are components of the red shellac obtained from the insect Kerria lacca , similar to carminic acid and kermesic acid. [1] This article focuses primarily on laccaic acid A (LCA). [2] [3]

Contents

Mixture of milk and lac dye - A ceremony welcoming the newly wed bride to her new home Feet-in-alta.jpg
Mixture of milk and lac dye - A ceremony welcoming the newly wed bride to her new home

History  

Etymology

The word varnish goes back to the old Indian Sanskrit word laksha, meaning a hundred thousand lice, and came into German via the Italian "lacca" in the 16th century. The word also exists in Hindi (Lakh) and Sinhala (Lakda). The term Lac Dye comes from English "dye" means paint dye. This pigment is mostly found in South and South-East Asia.

Usage

Laccaic acids are mainly used to dye natural fabrics (mostly silk, wool, or cotton) and food, including both drinks and solid products. [4] It is one of the most common natural dyes, but it is less used in cosmetics than carmine, the main natural dye used in this industry.  The bright red colorant gives a lightfast tint to silk and wool. It is a similar color to dyes obtained from cochineals and kermes. The color of the dye can be modified by the choice of mordant from violet to red to brown. The use of lac dye can be traced back to 250 AD when it was mentioned by Claudius Aelianus, a Roman writer on a volume about natural history. This pigment made from lac dye, Indian Lake, was listed by Winsor & Newton in their 1896 catalogue.  

Derivatives

These derivatives differ through one ramification except for the acid D, which is closer in form to the kermesic acid. Acid laccaic D can be confused or interchanged with flavokermisic acid due to their almost identical structure. [5] These acids can all be represented in a general form (lac-dye), where the derivative A is the most important.

The different derivatives include:

Acid B (3,5,6,8-tetrahydroxy-7-[2-hydroxy-5-(2-hydroxyethyl)phenyl]-9,10-dioxoanthracene-1,2-dicarboxylic acid) [6]

Acid C (7-[5-(2-amino-2-carboxyethyl)-2-hydroxyphenyl]-3,5,6,8-tetrahydroxy-9,10-dioxoanthracene-1,2-dicarboxylic acid) [7]

Acid D (3,6,8-trihydroxy-1-methyl-9,10-dioxoanthracene-2-carboxylic acid) [8]

Acid E (7-[5-(2-aminoethyl)-2-hydroxyphenyl]-3,5,6,8-tetrahydroxy-9,10-dioxoanthracene-1,2-dicarboxylic acid) [9]

Structure

Name Structure Molecular formula MW (g/mol) CAS number
Laccaic acid A Laccaic Acid A.svg C26H19NO12537.44 15979-35-8
Laccaic acid B Laccaic Acid B.svg C24H16O12496.38 17249-00-2
Laccaic acid C Laccaic Acid C.svg C25H17NO13539.41 23241-56-7
Laccaic acid D Laccaic Acid D.svg C16H10O7314.25 18499-84-8
Laccaic acid E Laccaic Acid E.svg C24H17NO11495.40 14597-16-1

Mixture of laccaic acid A-E: CAS 60687-93-6

Laccaic acid A has an amide functional group in its structure while the acids B, C, and E have amine groups. [10] The only difference between the acid D and kermesic acid is a hydroxide function missing on the position 8.

Isolation/extraction

A picture of Kerria lacca 02-Indian-Insect-Life - Harold Maxwell-Lefroy - Kerria-Lacca.jpg
A picture of Kerria lacca

Acids A, B, C, and E can be isolated from lac dye through many different ways: microwave induced from lac insects, high speed counter-current chromatography or liquid chromatography-mass spectrometry. [11] [12] [13]

Extraction from the stick lac

Stick lac next to colored silk strings Lac as a natural dye.jpg
Stick lac next to colored silk strings

The stick lac collected from Rain trees (mostly located in Asia) can be powdered in a mill and finely ground. The powdered material is extracted with deionized water at 60°C for 1 h. The aqueous solution is filtered and then concentrated under reduced pressure in a rotary evaporator to give a crude lac dye extract, which can then be used without further purification. This extract can be directly named lac dye. [14]

Biochemical properties

DNMT1 is inhibited by LCA which has a stronger inhibitory effect than SG-1027 (HY-13962). LCA is a class of DNMT inhibitors may be a useful mechanism to inhibit DNMT. [15]

Use

 As a major component of lac dye, LCA is usually chosen as a representative for the lac dye to describe their thermodynamics properties including adsorption, dyeability, fastness and shade variation of lac dyeing on silk and cotton. Studies indicate that the intermolecular interactions between LCA and fibers as well as between LCA and mordants play a key role on the adsorption and dyeability of lac dye. [16] [17]

Dyeing fabric

Lac extract produces purple colors. Lac is not so fast in cellulose fibers (plant fibers). Lac is very sensitive to pH, increasing alkalinity will turn the colors plummy purple, while acidity will give bright oranges. However, colors that have been altered by the pH change may turn red again after washing.

References

  1. ↑ PubChem. "Kermesic Acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-03-28.
  2. ↑ PubChem. "Laccaic acid A". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-03-27.
  3. ↑ "laccaic acid A | C26H19NO12 | ChemSpider". www.chemspider.com. Retrieved 2023-03-27.
  4. ↑ Park, Jin-Sung; Kim, Seung-Hyun; Kim, Yun-Soon; Kwon, Euna; Lim, Hyun-Jin; Han, Kang-Min; Choi, Yang-Kyu; Jung, Chul-Woo; Kang, Byeong-Cheol (2022-10-31). "Nonclinical safety evaluation of food colorant lac dye via systematic toxicity profiling with assessment of in vivo antigenic potential". Frontiers in Pharmacology. 13 1020379. doi: 10.3389/fphar.2022.1020379 . ISSN   1663-9812. PMC   9662299 . PMID   36386152.
  5. ↑ Wouters, Jan; Verhecken, André (1987-01-01). "The chemical nature of flavokermesic acid" . Tetrahedron Letters. 28 (11): 1199–1202. doi:10.1016/S0040-4039(00)95325-5. ISSN   0040-4039.
  6. ↑ PubChem. "Laccaic acid B". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-03-28.
  7. ↑ PubChem. "Laccaic acid C". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-03-28.
  8. ↑ PubChem. "Laccaic acid D". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-03-28.
  9. ↑ PubChem. "Laccaic acid E". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-03-28.
  10. ↑ Cooksey, C. J. (2019-02-17). "The red insect dyes: carminic, kermesic and laccaic acids and their derivatives" . Biotechnic & Histochemistry. 94 (2): 100–107. doi:10.1080/10520295.2018.1511065. ISSN   1052-0295. PMID   30354531. S2CID   53023592.
  11. ↑ Oka, Hisao; Ito, Yuko; Yamada, Sadaji; Kagami, Tadaaki; Hayakawa, Junko; Harada, Ken-ichi; Atsumi, Eiichiro; Suzuki, Masanao; Suzuki, Makoto; Odani, Hiroko; Akahori, Setsuko; Maeda, Kenji; Nakazawa, Hiroyuki; Ito, Yoichiro (1998-07-10). "Separation of lac dye components by high-speed counter-current chromatography" . Journal of Chromatography A. 813 (1): 71–77. doi:10.1016/S0021-9673(98)00311-2. ISSN   0021-9673. PMID   9697316.
  12. ↑ Ghosh, Manik; Dey, Suddhasattya (2019-10-14). "Bioactivity-guided isolation of Laccaic Acid-A: A potent anti-cancer agent from Laccifer lacca (Kerr)". Indian Journal of Traditional Knowledge. 18 (4): 677–685. doi:10.56042/ijtk.v18i4.28998 (inactive 12 July 2025). ISSN   0975-1068.{{cite journal}}: CS1 maint: DOI inactive as of July 2025 (link)
  13. ↑ Adeel, Shahid; Hussaan, Muhammad; Rehman, Fazal-ur; Habib, Noman; Salman, Mahwish; Naz, Saba; Amin, Nimra; Akhtar, Nasim (2018-03-20). "Microwave-assisted sustainable dyeing of wool fabric using cochineal-based carminic acid as natural colorant". Journal of Natural Fibers. 16 (7): 1026–1034. doi:10.1080/15440478.2018.1448317. ISSN   1544-0478. S2CID   139302709.
  14. ↑ Dingyu Hu; Akira Hasegawa; Shin-ichi Nakatsuka (1997-08-01). "Isolation and Structure Determination of Laccaic Acid F from Lac-Dye Produced from Thai Sticklac". Heterocyclic Communications. 3 (4): 327–330. doi: 10.1515/HC.1997.3.4.327 . ISSN   2191-0197. S2CID   92700927.
  15. ↑ Fagan, Rebecca L.; Cryderman, Diane E.; Kopelovich, Levy; Wallrath, Lori L.; Brenner, Charles (16 August 2013). "Laccaic Acid A Is a Direct, DNA-competitive Inhibitor of DNA Methyltransferase 1 *". Journal of Biological Chemistry. 288 (33): 23858–23867. doi: 10.1074/jbc.M113.480517 . ISSN   0021-9258. PMC   3745332 . PMID   23839987. Creative Commons by small.svg  This article incorporates textfrom this source, which is available under the CC BY 4.0 license.
  16. ↑ Kongkachuichay, Paisan; Shitangkoon, Aroonsiri; Chinwongamorn, Nontalee (2002-05-01). "Thermodynamics of adsorption of laccaic acid on silk" . Dyes and Pigments. 53 (2): 179–185. doi:10.1016/S0143-7208(02)00014-1. ISSN   0143-7208.
  17. ↑ "Material-Archiv". materialarchiv.ch. Retrieved 2023-03-27.
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