Determine the necessary mass, volume, or concentration for preparing a solution.
≥97% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -20°C Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 25 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
A 12-hydroxy fatty acid that can be a used as a substrate for conjugated linoleic acid synthesis.
| Canonical Smiles | CCCCCCC(CC=CCCCCCCCC(=O)O)O |
|---|---|
| IUPAC Name | (Z,12R)-12-hydroxyoctadec-9-enoic acid |
| InChIKey | WBHHMMIMDMUBKC-QJWNTBNXSA-N |
| INCHI | 1S/C18H34O3/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21/h9,12,17,19H,2-8,10-11,13-16H2,1H3,(H,20,21)/b12-9-/t17-/m1/s1 |
| Isomeric SMILES | CCCCCC[C@H](C/C=C\CCCCCCCC(=O)O)O |
| WGK Germany | 3 |
| RTECS | VJ3150000 |
| Molecular Weight | 298.46 |
| Beilstein | 1727813 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lipids and lipid-like molecules |
| Class | Fatty Acyls |
| Subclass | Fatty acids and conjugates |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Long-chain fatty acids |
| Alternative Parents | Hydroxy fatty acids Unsaturated fatty acids Secondary alcohols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Long-chain fatty acid - Hydroxy fatty acid - Unsaturated fatty acid - Secondary alcohol - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Alcohol - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. |
| External Descriptors | Other Octadecanoids |
Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Date | Item |
|---|---|---|---|
| Certificate of Analysis | Sep 28, 2025 | R1456165 |
| Solubility | Soluble in water (3.46 mg/ml), chloroform, acetone, alcohol, and ether. |
|---|---|
| Flash Point(°F) | 435.2℉ |
| Flash Point(°C) | 224 ℃ |
| Boil Point(°C) | 245°C |
| Melt Point(°C) | 5.5°C |
| Molecular Weight | 298.500 g/mol |
| XLogP3 | 5.700 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 15 |
| Exact Mass | 298.251 Da |
| Monoisotopic Mass | 298.251 Da |
| Topological Polar Surface Area | 57.500 Ų |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Complexity | 261.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 1 |
| Covalently-Bonded Unit Count | 1 |
| 1. Yuanchuan Ma, Jiao Wei, Jialong Zhu, Yang Hu, Yuquan Cai, Jieyuan Zheng, Hong Fan. (2023) Novel ricinoleic acid highly functionalized hierarchical SiO2 with switchable superwettability for removal of oils, heavy metal ions, and organic dyes from water. APPLIED SURFACE SCIENCE, [PMID:] [10.1016/j.apsusc.2023.158238] |
| 2. Meng Zhang, QingYan Li, Feiyu Fan, Fuping Lu, XueLi Zhang. (2023) Combinatorial metabolic engineering and tolerance evolution of Yarrowia lipolytica for improved γ-decalactone synthesis. PROCESS BIOCHEMISTRY, [PMID:] [10.1016/j.procbio.2023.07.021] |
| 3. Heng Li, Fang-Yu Ren, Hong-Ru Li, Liang-Nian He. (2023) Modification of ricinoleic acid based nonisocyanate polyurethane using polyamine containing polyhedral oligomeric silsesquioxane. POLYMER ENGINEERING AND SCIENCE, 63 (5): (1507-1515). [PMID:] [10.1002/pen.26301] |
| 4. Fen Xu, Shiwei Wang, Rongjie Kong, Chengyong Wang. (2023) Synergistic effects of dodecane-castor oil acid mixture on the flotation responses of low-rank coal: A combined simulation and experimental study. International Journal of Mining Science and Technology, [PMID:] [10.1016/j.ijmst.2022.11.010] |
| 5. Wei-Wei Ye, Xiang-Ying Meng, Qian Zhao, Jian-Yang Chen, Cong Liu, Feng Chen, Yong Zhou, Yi Wang. (2022) Echinacoside exerts its protective effects in a type 2 diabetes mellitus injury model via the AKT pathway. JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, [PMID:36573490] [10.1080/10286020.2022.2157269] |
| 6. Fengchang Huang, Xiaoming Mo, Xuesong Li, Maolan Peng, Yulu Zhou, Xiaoma Tao, Yifang Ouyang, Jialong Zhao. (2022) Improved efficiency for lead-free CsCu2I3 halide microplatelets by suppressing surface pinholes via surface functionalization. JOURNAL OF LUMINESCENCE, [PMID:] [10.1016/j.jlumin.2022.119390] |
| 7. Yang Yang, Caili Zhang, Yu Han, Yunxuan Weng. (2022) Plasticizing and thermal stabilizing effect of bio-based epoxidized cardanol esters on PVC. POLYMERS FOR ADVANCED TECHNOLOGIES, 34 (1): (181-194). [PMID:] [10.1002/pat.5876] |
| 8. Yuehong Zhang, Chenyang Liu, Jianzhong Ma, Wenbo Zhang, Qianqian Fan, Zhonglei Ma. (2022) Relationship between the Structure of Modified Ricinoleic Acids via the Thiol–Ene Click Reaction and the Fogging Value of Fatliquored Leather. ACS Sustainable Chemistry & Engineering, [PMID:] [10.1021/acssuschemeng.2c02364] |
| 9. Hongzhi Liu, Ning Chen, Changqing Peng, Shuai Zhang, Tuan Liu, Pingan Song, Guolun Zhong, Hao Liu. (2022) Diisocyanate-Induced Dynamic Vulcanization of Difunctional Fatty Acids toward Mechanically Robust PLA Blends with Enhanced Luminescence Emission. MACROMOLECULES, [PMID:] [10.1021/acs.macromol.2c00674] |
| 10. Baozhong Zhu, Weiqi Chen, Yunlan Sun, Peng Guo, Jianzhong Liu. (2021) Experimental study on the evaporation and combustion characteristics of double Al/n-heptane based nanofluid fuel droplets in high temperature environment. THERMOCHIMICA ACTA, [PMID:] [10.1016/j.tca.2021.179049] |
| 11. Lin Yamei, Li Mei, Xia Jianling, Ding Haiyang, Xu Lina, Yang Xiaohua, Li Shouhai. (2021) Synthesis of plant oil derived polyols and their effects on the properties of prepared ethyl cellulose composite films. CELLULOSE, 28 (7): (4211-4222). [PMID:] [10.1007/s10570-021-03811-z] |
| 12. Haifei Zhang, Fengfan Zhu, Qinghe Fu, Xiaoxiang Zhang, Xinbao Zhu. (2019) Mechanical properties of renewable plasticizer based on ricinoleic acid for PVC. POLYMER TESTING, [PMID:] [10.1016/j.polymertesting.2019.03.020] |
| 13. Mei Li, Jianling Xia, Chengxiang Ding, Wei Mao, Haiyang Ding, Lina Xu, Shouhai Li. (2017) Development and characterization of ricinoleic acid-based sulfhydryl thiol and ethyl cellulose blended membranes. CARBOHYDRATE POLYMERS, [PMID:28917848] [10.1016/j.carbpol.2017.07.069] |
| 14. Mei Li, Jianling Xia, Wei Mao, Xuejuan Yang, Lina Xu, Kun Huang, Shouhai Li. (2017) Preparation and Properties of Castor Oil-Based Dual Cross-Linked Polymer Networks with Polyurethane and Polyoxazolidinone Structures. ACS Sustainable Chemistry & Engineering, [PMID:] [10.1021/acssuschemeng.7b01103] |
| 15. Xuejuan Yang, Chunpeng Wang, Jianling Xia, Wei Mao, Shouhai Li. (2017) Study on synthesis of novel phosphorus-containing flame retardant epoxy curing agents from renewable resources and the comprehensive properties of their combined cured products. PROGRESS IN ORGANIC COATINGS, [PMID:] [10.1016/j.porgcoat.2017.01.012] |
| 16. Jun Cao, Meng Yang, Fuliang Cao, Jiahong Wang, Erzheng Su. (2017) Tailor-made hydrophobic deep eutectic solvents for cleaner extraction of polyprenyl acetates from Ginkgo biloba leaves. Journal of Cleaner Production, [PMID:] [10.1016/j.jclepro.2017.03.140] |
| 17. Chen Jiang, Yuyun Lu, Zhuo Li, Cunzhi Li, Rian Yan. (2016) Enzymatic Synthesis of l-Ascorbyl Fatty Acid Esters Under Ultrasonic Irradiation and Comparison of Their Antioxidant Activity and Stability. JOURNAL OF FOOD SCIENCE, 81 (6): (C1370). [PMID:27100741] [10.1111/1750-3841.13317] |
| 18. Shangde Sun, Xulei Li. (2016) Functional Ionic Liquids Catalyzed the Esterification of Ricinoleic Acid with Methanol to Prepare Biodiesel: Optimization by Response Surface Methodology. JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 93 (6): (757-764). [PMID:] [10.1007/s11746-016-2826-5] |
| 19. Benzhao He, Li Zhou. (2015) Efficient tailoring of the surface of upconversion nanoparticles via surface-initiated cationic ring-opening polymerization. RSC Advances, 5 (118): (97764-97772). [PMID:] [10.1039/C5RA18922E] |
| 20. Zhang Yulong, Xu Zhizhen, Sun Huanghui, Qiu Qiaoli, Zhang Lingfan, Xia Wei, Zhang Wenqing. (2015) Fabrication of Pd-loaded carbon spheres with magnetic properties as active catalysts. APPLIED PHYSICS A-MATERIALS SCIENCE & PROCESSING, 119 (2): (603-608). [PMID:] [10.1007/s00339-015-8998-2] |
| 21. Li Zhou, Benzhao He, Jiachang Huang, Zehong Cheng, Xu Xu, Chun Wei. (2014) Multihydroxy Dendritic Upconversion Nanoparticles with Enhanced Water Dispersibility and Surface Functionality for Bioimaging. ACS Applied Materials & Interfaces, [PMID:24749852] [10.1021/am500980z] |
| 22. Zhuangzhuang Xiong, Ziheng Qi, Wenhui Zhang, Mingbo Ji, Fuqiu Ma, Lixia Ying, Guixiang Wang. (2024) Enhancing frictional and corrosion resistance performance in aluminum alloy through in situ growth of NiZnAl-LDH membrane and its modification. Surfaces and Interfaces, [PMID:] [10.1016/j.surfin.2024.104103] |
| 23. Hang Shen, Jianfu Chen, Kok Bing Tan. (2024) Ethyl cellulose matrixed poly(sulfur-co-sorbic acid) composite films: Regulation of properties and application for food preservation. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, [PMID:39214227] [10.1016/j.ijbiomac.2024.135183] |
| 24. Chunfei Zhong, Xinyan Li, Fan Zhang, Ning Liu, Jiewei Deng, Yunyun Yang, Tiangang Luan. (2024) Rapid and sensitive determination of bongkrekic acid with molecularly imprinted polymer-coated wooden-tip electrospray ionization mass spectrometry. Advances in Sample Preparation, [PMID:] [10.1016/j.sampre.2024.100137] |
| 25. Yike Guo, Song Yang, Pengwei Ren, Hao Liu, Xuemei Miao, Zhenjiang Wu, Yantong Lv, Ju ShangGuan, Yadong Bai. (2025) Interfacial self-healing lubrication in pen nib steel: Water-based composite nanoparticle lubricants for friction reduction. COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS, [PMID:] [10.1016/j.colsurfa.2025.137087] |