Basic information
- CAS
301-02-0- Standard SMILES
CCCCCCCC/C=C\CCCCCCCC(N)=O- InChIKey
FATBGEAMYMYZAF-KTKRTIGZSA-N- Molecular formula
- C18H35NO
- Average molar mass
- 281.5 g/mol
- Monoisotopic mass
- 281.27186474
Names & identifiers
- Preferred name
- Oleamide
- IUPAC
- (Z)-octadec-9-enamide
- English name
- Oleamide
- Molecular formula
- C18H35NO
- Molecular weight
- 281.48
Names & synonyms
Oleamide301-02-0Oleic acid amideOleylamideOleyl amide(Z)-octadec-9-enamideAdogen 739-Octadecenamide, (9Z)-Crodamide OCrodamide ORSlip-ezeArmoslip CP
Show more names
ODA9-OCTADECENAMIDEOLEAMIDCIS-9-OCTADECENAMIDE9-Octadecenamide,(Z)-(9Z)-9-Octadecenamide
(Z)-9-OCTADECENAMIDE9Z-octadecenamideArmid O9,10-octadecenamide7L25QK8BWONSC-26987CHEBI:116314RefChem:856476
Database identifiers
- CAS
301-02-0- PubChem CID
- 5283387
- DTXSID
DTXSID6027137- ChEMBL
CHEMBL15927- ChEBI
CHEBI:116314- UNII
- 7L25QK8BWO
- EC Number
- 206-103-9
- Nikkaji
- J36.613G
Properties
Computed structural properties
- XLogP
- 6.6
- Topological polar surface area
- 43.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 15
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 236
Experimental & physicochemical properties
Density0.94
Color/FormIVORY-COLORED POWDER
SolubilityINSOL IN WATER; SOL IN ETHER, HOT ALCOHOL
Melting Point
76 °C
102 - 104 °C
Vapor Pressure0.0000012 [mmHg]
Physical Description
Large Crystals; Dry Powder; Liquid; Dry Powder; Large Crystals; Other Solid; Dry Powder; Large Crystals
Ivory-colored solid; [HSDB]
Solid
Kovats Retention Index
2375；2397
3265
Physicochemical properties
- Melting point
- 70 °C · 70°C
- Boiling point
- 433.3 · 433.3±24.0 °C(Predicted)
- Density
- 0.94 g/cm3 · 0.94 g/cm3
- storage temp.
- -20 °C · -20°C
- solubility
- Soluble in chloroform (50 mg/ml), ethanol (100 mM), DMSO (~14 mg/ml), and DMF (~14 mg/ml)
- pka
- 16.61 · 16.61±0.40(Predicted)
- form
- Solid
- color
- White to off-white
- Water Solubility
- Insoluble in water.
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
- Cosmetics Ingredients Functions
- OPACIFYINGVISCOSITY CONTROLLING
- InChI
- 1S/C18H35NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H2,19,20)/b10-9-
- InChIKey
- FATBGEAMYMYZAF-KTKRTIGZSA-N
- SMILES
- CCCCCCCC\C=C/CCCCCCCC(N)=O
- LogP
- 6.882 · 6.882 (est)
- CAS DataBase Reference
- 301 · 301-02-0(CAS DataBase Reference)
- Indirect Additives used in Food Contact Substances
- OLEAMIDE
- FDA 21 CFR
- 175.105 · 175.105; 175.300; 178.3910;179.45; 181.28
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 7 L25QK8BWO · 7L25QK8BWO
- NIST Chemistry Reference
- 9 · 9-Octadecenamide, (z)-(301-02-0)
- EPA Substance Registry System
- Oleamide (301-02-0)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 413 · H413
- Precautionary statements
- 273 · P273-P501
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38-43
- Safety Statements
- 26 · 26-36-37
- WGK Germany
- 1 · 1
- TSCA
- TSCA listed
- HS Code
- 29241990 · 29241990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 · Aquatic Chronic 4
- Hazardous Substances Data
- 301 · 301-02-0(Hazardous Substances Data)
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 42.7% (470 of 1101) of reports.
Warning
H315 (12.1%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (12.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (12.1%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]；H413 (40.2%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]
P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1101 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 470 of 1101 reports by companies.；There are 7 notifications provided by 631 of 1101 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory Information
Chemical: 9-Octadecenamide, (Z)-
9-Octadecenamide, (9Z)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 9-Octadecenamide, (9Z)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
9-Octadecenamide, (9Z)-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 9-Octadecenamide, (Z)-: Human health tier I assessment
Hazards Summary
Contact urticarial reaction reported within 20 minutes of open patch test; Emergency treatment: Irritants; [HSDB] Causes mild skin and eye irritation in rabbits; Not considered sensitizing to human skin; [IUCLID] Causes changes in motor activity and excitement in acute intraperitoneal toxic-dose studies of rats and mice; [RTECS] A skin and strong eye irritant; May cause an allergic skin reaction; [Aldrich MSDS]
Hazard Classes and Categories
Skin Irrit. 2 (12.1%)；Eye Irrit. 2 (12.1%)；STOT SE 3 (12.1%)；Aquatic Chronic 4 (40.2%)
Serious eye damage/eye irritation - Category 2B
Toxicology
Human Toxicity ExcerptsOPEN PATCH TEST WITH OLEYLAMIDE (AMIDE OF OLEIC ACID) 0.1% IN ETHANOL ELICITED A STRONG URTICARIAL REACTION IN 20 MIN.
Regulatory information
Regulatory Information
Chemical: 9-Octadecenamide, (Z)-
9-Octadecenamide, (9Z)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 9-Octadecenamide, (9Z)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
9-Octadecenamide, (9Z)-: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 1
- tsca
- TSCA listed
- hs_code
- 29241990
- risk_code
- 36/37/38-43
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36-37
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H413
- Hazard Classifications
- Aquatic Chronic 4
- Precautionary statements
- P273-P501
- Hazardous Substances Data
- 301-02-0(Hazardous Substances Data)
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances used in the processing or storage of foods or animal feed including ANTIOXIDANTS; FOOD PRESERVATIVES; FOOD COLORING AGENTS; FLAVORING AGENTS; ANTI-INFECTIVE AGENTS; EXCIPIENTS and other similarly used substances. Many of the same substances are used as PHARMACEUTIC AIDS.
Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
Cellular LocationsExtracellular；Membrane
Uses & manufacturing
Uses
Used as a slip and anti-block agent for extrusion of polyethylene and an additive to wax, printing inks, lubricating oils, and cosmetics; [HSDB] Used as a rubber additive, anti-static agent, dispersion aid, and mold release agent; [IUCLID]
Molding and Core Making [Category: Foundry]
SLIP-AGENT FOR EXTRUSION OF POLYETHYLENE; WAX ADDITIVE; INK ADDITIVE; COSMETICS
SLIP & ANTIBLOCK AGENT FOR PLASTICS-ESP POLYETHYLENE FILM
LUBRICATING OIL ADDITIVE
PRINTING INK ADDITIVE
U.S. Exports
(1979) No Data
(1981) No Data
U.S. Imports
(1979) No Data
(1981) No Data
U.S. Production
2023: 7,000,000 - <8,500,000 lb；2022: 10,000,000 - <25,000,000 lb；2021: 10,000,000 - <25,000,000 lb；2020: 10,000,000 - <25,000,000 lb
(1980) 2.27X10+9 GRAMS (ESTIMATE)
(1981) PROBABLY GREATER THAN 6.81X10+6 GRAMS
Consumer UsesLubricating agent；Anti-adhesive/cohesive；Surface modifier
Industry UsesAnti-adhesive/cohesive；Lubricating agent；Anti-slip agent；Adhesion/cohesion promoter；Anti-scaling agent；Surface modifier
Methods of ManufacturingREACTION OF (Z)-9-OCTADECENOIC ACID WITH ANHYDROUS AMMONIA
Use ClassificationCosmetics -> Opacifying; Viscosity controlling
General Manufacturing Information
Plastics Material and Resin Manufacturing；Paint and Coating Manufacturing；Adhesive Manufacturing；All Other Chemical Product and Preparation Manufacturing；Rubber Product Manufacturing；Custom Compounding of Purchased Resins；Petroleum Lubricating Oil and Grease Manufacturing；Synthetic Rubber Manufacturing；Plastics Product Manufacturing；Wholesale and Retail Trade
9-Octadecenamide, (9Z)-: ACTIVE
ADOGEN /IS/ TRADEMARK FOR SERIES OF FATTY NITROGEN CHEM INCL AMINES, AMIDES... AVAIL IN VARIOUS GRADES FOR SPECIFIC APPLICATIONS IN FABRIC SOFTENERS, ORE SEPARATION, DETERGENTS, PETROLEUM ADDITIVES, CORROSION INHIBITORS, BACTERICIDES, PRINTING INKS, ANTIBLOCK & SLIP AGENTS... /ADOGEN/
SLIP-EZE /IS/ TRADEMARK FOR A SPECIALLY PREPARED FATTY ACID AMIDE. USED AS SLIP ADDITIVE & AS INTERNAL MOLD-RELEASE ADDITIVE TO POLYETHYLENE.
Applications
UsesThe purpose is as following: 1, it is the chemical additives which must been added to the low-density polyethylene (LDPE) film material. 2, it is also the modifying agent of the plastic ink. 3, it can also be used as the lubricants such as polypropylene (PP), polystyrene (GPPS), phenol (PF) resin, antistatic agents and anti-caking additives. 4, it can also be used as polyethylene, polypropylene, synthetic fibers and other color concentrates and cables (insulation) material lubricant and release agent. 5, it can also be used as the additive for polypropylene (seal) tabletting, efficient heat sheet and sealed material. 6, metal protective agent; stabilizer of the melamine tableware products; lubricants, antifreeze additives of the brake; lubricants of the coatings and dispersion stabilizer of the aluminum coating as well as oil drilling auxiliaries.
DescriptionOOleamide (301-02-0) was originally identified in the cerebrospinal fluid of sleep-deprived cats acting as an inducer of physiological sleep in animals.1 Displays agonist activity at cannabinoid CB1 receptors (Ki=8.13 μM).2 Activates PPARγ.3 Produces vasodilator effects in rats.4 Displays neuroprotective effects5 and attenuates sepsis-induced intestinal injury6.
UsesA brain lipid that induces physiological sleep at nanomolar quantities when injected into rats. This lipid may represent a new class of biological signaling molecules.
UsesOleamide has been used as a supplement in glucose and galactose media to prevent the rescue of galactose-induced Leigh syndrome (LS).
General DescriptionOleamideis a lipid or a brain fatty acid, that is found in the CSF (cerebrospinal fluid). It is originally obtained from the cerebrospinal fluid of cats, that are sleep-deprived.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖南长沙恒昌化工有限公司0731-85070388 13217318550
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]
宜昌众意泰贸易有限公司0717-6449896 13886658719 · [email protected]
Syntechem Co.,Ltd[email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
安耐吉化学&3A（安徽泽升科技股份有限公司）400-0056266 · [email protected]
山东洛克化工有限公司17653113209 13065062079 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
上海钰康生物科技有限公司+86-18930848214 +86-021-56762820 · [email protected]
上海相辉医药科技有限公司13761987713 · [email protected]
上海隆盛化工有限公司58099637 13585536065 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
玛雅试剂+86 (573) 82222445 (0)18006601000 452520369 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
Connect Chemicals GmbH+49 2102 2077 19 · [email protected]
斯百全化学（上海）有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
上海遐瑞医药科技有限公司+86 21 61551611
江苏艾康生物医药研发有限公司025-66113011 13913916777 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
上海贺康生物技术有限公司17721021104 18939837085 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
安徽科迪达化工有限公司0554-2106669 · [email protected]
江西智联新材料有限公司13507965277 13507965277 · [email protected]
日照力德士化工有限公司010-51268198 · [email protected]
美岚实业（上海）有限公司021-58958189 · [email protected]
上海爱蝶实业有限公司021-58957966 18930537195 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
广拓化学（上海）有限公司021-60899189-8001 18918189673 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
Shenzhen Vtolo Chemicals Co., Ltd.13534282526 · [email protected]
成都润泽本土化工有限公司13096311329 028-88469284 616445927 · [email protected]
凯试（上海）科技有限公司021-50135380 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
TargetMol中国（陶术生物）021-021-33632979 15002134094 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
Additional notes
DefinitionChEBI: A fatty amide derived from oleic acid.
Related reactions
3 records
Compound notes
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