japanic acid
{{Chembox
| Name = Japanic acid
| ImageFile = Japanic acid v2.svg
| ImageSize = 200px
| ImageAlt =
| IUPACName = japonic acid,{{cite web |title=PlantFAdb: 20-COOH-20:0; Heneicosanedioic acid; Japonic acid; Japanic acid |url=https://plantfadb.org/fatty_acids/10248 |publisher=plantfadb.org |access-date=1 April 2025}} heneicosanedioic acid
| OtherNames =
| Section1 = {{Chembox Identifiers
| CASNo = 505-55-5
| CASNo_Ref = {{Cascite|changed|CAS}}
| ChemSpiderID = 7822618
| ChEBI = 165385
| DTXSID =
| EC_number =
| UNII = 73CA8QKN34
| PubChem = 9543668
| InChI = InChI=1S/C21H40O4/c22-20(23)18-16-14-12-10-8-6-4-2-1-3-5-7-9-11-13-15-17-19-21(24)25/h1-19H2,(H,22,23)(H,24,25)
| InChIKey = PWLXTFFHCFWCGG-UHFFFAOYSA-N
| SMILES = C(CCCCCCCCCC(=O)O)CCCCCCCCCC(=O)O
}}
| Section2 = {{Chembox Properties
| H=40|O=4|C=21
| MolarMass =
| Appearance = brown solid
| Density =
| MeltingPt = 117.5–117.9 °C
| BoilingPt =
| Solubility = poorly soluble
}}
| Section3 = {{Chembox Hazards
| GHSPictograms =
| GHSSignalWord =
| GHS_ref =
| HPhrases =
| PPhrases =
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
Japanic acid or heneicosanedioic acid is a chemical compound with the chemical formula {{chem2|НООС(СН2)19СООН}}.
The compound is a long-chain dicarboxylic acid, one of the longest naturally occurring dicarboxylic acids. Initially, it was extracted from natural fat called Japan wax.{{cite book |last1=Krendlinger |first1=Ernst J. |last2=Wolfmeier |first2=Uwe H. |title=Natural and Synthetic Waxes: Origin, Production, Technology, and Applications |date=31 October 2022 |publisher=John Wiley & Sons |isbn=978-3-527-80776-5 |page=229 |url=https://books.google.com/books?id=k1qZEAAAQBAJ&dq=Japanic+acid&pg=PA229 |access-date=1 April 2025 |language=en}}{{cite book |last1=Whitmore |first1=Frank C. |title=Organic Chemistry, Volume One: Part I: Aliphatic Compounds Part II: Alicyclic Compounds |date=13 November 2012 |publisher=Courier Corporation |isbn=978-0-486-31115-9 |page=386 |url=https://books.google.com/books?id=6W_CAgAAQBAJ&dq=%22japanic+acid%22&pg=PA386 |access-date=1 April 2025 |language=en}}{{cite book |last1=Singh |first1=Bharat P. |title=Industrial Crops and Uses |date=2010 |publisher=CABI |isbn=978-1-84593-616-7 |page=416 |url=https://books.google.com/books?id=I1j2ZtzZXgUC&dq=Japanic+acid&pg=PA416 |access-date=1 April 2025 |language=en}}
Dicovery
Japanic acid was first isolated by Eberhardt in 1888 by fractional distillation under vacuum.{{cite book |title=Journal of the Chemical Society (Great Britain) |date=1908 |publisher=Chemical Society |page=5 |url=https://books.google.com/books?id=7nDymnSWhmYC&dq=eberhardt+Strassburg++1888&pg=PA5-IA6 |access-date=1 April 2025 |language=en}}
Since the natural raw material from which the acid is obtained was the dried juice of some species of acacia trees (catechu), called "Japanese dirt", and the acid was called Japanic.{{cite book |last1=Леенсон |first1=Илья |title=Язык химии. Этимология химических названий |date=14 October 2016 |publisher=Litres |isbn=978-5-04-030122-5 |page=433 |url=https://books.google.com/books?id=BmJDDQAAQBAJ&dq=%D1%8F%D0%BF%D0%BE%D0%BD%D0%BE%D0%B2%D0%B0%D1%8F+%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0&pg=PT221 |access-date=1 April 2025 |language=ru}}
Physical properties
Like other long-chain dicarboxylic acids, it demonstrates physical properties typical of fatty acids with extended carbon backbones, including high melting points and limited water solubility.
Japanic acid melts at a temperature of 117.5–117.9 °C. When heated to 200 °C, it begins to decompose with the release of {{CO2}} and the formation of ketone {{chem2|C10H21COC10H21}}.
The acid and its salts are colored in various shades of brown. The acid is only slightly soluble in most solvents.
Uses
Japanic acid is used in the synthesis of polyesters.{{cite journal |last1=Birkle |first1=Melissa |last2=Mehringer |first2=Hannah S. |last3=Nelson |first3=Taylor F. |last4=Mecking |first4=Stefan |title=Aliphatic Polyester Materials from Renewable 2,3-Butanediol |journal=ACS Sustainable Chemistry & Engineering |date=11 March 2024 |volume=12 |issue=10 |pages=4156–4163 |doi=10.1021/acssuschemeng.3c07665 |doi-access=free }}