(9Z)-12-hydroxyoctadec-9-enoic acid

Base Information

• Chemical Name: (9Z)-12-hydroxyoctadec-9-enoic acid
• CAS No.: 141-22-0
• Molecular Formula: C18H34O3
• Molecular Weight: 298.466
• Hs Code.: 29181990
• NSC Number: 281242
• Nikkaji Number: J254.330C
• Wikidata: Q27158675
• Mol file: 141-22-0.mol

Synonyms:12-D-hydroxy-9-trans-octadecenoic acid;12-hydroxy-9-octadecenic acid;12-hydroxy-9-octadecenoic acid;12-hydroxyoctadec-cis-9-enoic acid;9-octadecenoic acid, 12-hydroxy-, (9E,12R)-;ricinelaidic acid;ricinoleic acid;ricinoleic acid, (R-(E))-isomer

Chemical Property of (9Z)-12-hydroxyoctadec-9-enoic acid

Chemical Property:

• Appearance/Colour: yellow viscous liquid
• Vapor Pressure: 1.12E-08mmHg at 25°C
• Melting Point: 〈10oC
• Refractive Index: 1.4740 (589.3 nm, 25℃)
• Boiling Point: 416.4 °C at 760 mmHg
• PKA: 4.78±0.10(Predicted)
• Flash Point: 219.8 °C
• PSA: 57.53000
• Density: 0.957 g/cm³
• LogP: 5.07930
• Storage Temp.: 2-8°C
• Solubility.: Ethanol
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 15
• Exact Mass: 298.25079494
• Heavy Atom Count: 21
• Complexity: 261

Purity/Quality:

99% ^*data from raw suppliers

RicinolicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC(CC=CCCCCCCCC(=O)O)O
• Isomeric SMILES: CCCCCCC(C/C=C\CCCCCCCC(=O)O)O
• Description: Ricinoleic acid is an unsaturated omega-9 fatty acid and is an important component of the seed oil obtained from mature castor plants seeds. The compound is produced for industries by fractional distillation or saponification of hydrolysed castor oil. It is normally used in manufacturing personal care products such as deodorants. Much of ricinoleic acid characteristics and effects can be associated with castor oil.
• Uses: Soaps, Turkey red oil, textile finishing, source of sebacic acid and heptanol, ricinoleate salts, 12- hydroxystearic acid. soaps: Ricinoleic acid can be reacted with various bases (caustic, ammonia, ethanolamines, etc.) to produce soaps having the desired characteristics (solubility, physical characteristics, polarity, etc.) depending on the final application. Some of them are: cutting oils, industrial lubricants, emulsifiers and metal working fluids. Transparent bar soaps & high solids liquids soaps are made possible by using Ricinoleic acid. The same for industrial germicides, disinfectants and heavy duty detergents (solubilization of phenolic and cresylic bodies). surface coating: it is used as an efficient pigment/dye dispersants in inks, coatings, plastics, cosmetics, etc. textiles: Ricinoleic acid provides polarity, surface wetting and lubricity. rubber: the sodium/potassium soaps of Ricinoleic acid are emulsifiers and foam stabilizers. vinyl polymers: it's sodium soap is useful as emulsifier, stabilizer and defoamer for emulsion polymerization of resins such as PVC & PVAc food additives: it's used in the production of PGPR (polyglycerol polyricinoleate) for use in chocolate. Ricinolic Acid is a metabolite of linoleic acid from Lactobacilli and has antifungal activity in bread. Ricinolic Acid is also a metabolite of castor oil and has shown to activate intestinal and uterine smooth-muscle cells through EP3 prostanoid receptors inducing diarrhea and labor in pregnant females.

Technology Process of (9Z)-12-hydroxyoctadec-9-enoic acid

There total 10 articles about (9Z)-12-hydroxyoctadec-9-enoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

[R-(Z)]-12-(acetyloxy)-9-octadecenoic acid methyl ester (140-03-4) → Ricinoleic acid (141-22-0,27925-02-6,7431-95-0,84799-84-8)

Guidance literature:

With lithium hydroxide; water; In tetrahydrofuran; for 6h; Ambient temperature;

DOI:10.1080/00397919908086253

Reference yield: 20.0%

methyl acetyl ricinoleate (41015-43-4) → Ricinoleic acid (141-22-0,27925-02-6,7431-95-0,84799-84-8) + methyl ricinoleate (41989-07-5) + (Z)-12-Acetoxy-octadec-9-enoic acid (111766-70-2)

Guidance literature:

With sodium hydroxide; In methanol; under 750.06 Torr;

DOI:10.1021/jo00020a001

Reference yield:

→ Ricinoleic acid (141-22-0,27925-02-6,7431-95-0,84799-84-8)

Guidance literature:

With alkaline solution;

upstream raw materials:

heptanal

10-undecenoic acid

methyl acetyl ricinoleate

[R-(Z)]-12-(acetyloxy)-9-octadecenoic acid methyl ester

Downstream raw materials:

methyl ricinoleate

12-hydroxy-9-octadecenoic acid ethyl ester

ethyl ricinoleate

ricinolic acid heptyl ester

Refernces

• 1、 Ewonkem, Monique B.,Grinberg, Sarina,Lemcoff, Gabriel,Shaubi, Eleonora,Linder, Charles,Heldman, Eliahu. "Newly synthesized bolaamphiphiles from castor oil and their aggregated morphologies for potential use in drug delivery". . p. 8557 - 8571. Retrieved 2015.
• 2、 Slivniak, Raia,Domb, Abraham J.. "Lactic acid and ricinoleic acid based copolyesters". . p. 5545 - 5553. Retrieved 2005.
• 3、 -. "Tailored Oils Produced from Recombinant Oleaginous Microorganisms". . . Retrieved 2012/08/27.