HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pimelic Acid
HEPTANEDIOIC ACID · Pimelate · PimeL · heptanedioate · 6-carboxyhexanoate · 1,5-PENTANEDICARBOXYLIC ACID · NSC-30112 · PiMelic aci
Identifiers & Physical Properties
| CAS No. | 111-16-0 |
|---|---|
| Molecular formula | C7H12O4 |
| Average molar mass | 160.17 g/mol |
| Monoisotopic mass | 160.07355886 g/mol |
| SMILES | O=C(O)CCCCCC(=O)O |
| InChIKey | WLJVNTCWHIRURA-UHFFFAOYSA-N |
| PubChem CID | 385 |
| ChEMBL | CHEMBL1235351 |
| ChEBI | CHEBI:30531 |
| EC No. | 203-840-8 |
| DTXSID | DTXSID5021598 |
Chemical & Physical Properties
| XLogP | 0.5 |
|---|---|
| Topological polar surface area | 74.6 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 4 |
| Rotatable bonds | 6 |
| Heavy atoms | 11 |
| Formal charge | 0 |
| Complexity | 125 |
| Chemical classes | Other Classes -> Organic Acids |
| Drugs | Pharmaceuticals -> Listed in ZINC15 |
| Lipids | Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Dicarboxylic acids [FA0117] |
| SpringerMaterials Properties | Boiling point |
| LogP (partition coefficient) | 0.61 |
| Plasticizers | Plasticizer |
| Solubility | 50.0 mg/mLethanol: 0.1 g/mL, clear to very faintly hazy25 g/L (13 ºC) |
| Boiling point | 342.00 °C. @ 760.00 mm Hg212 °C10 mm Hg(lit.) |
| Melting point | 103 - 106 °C103-105 °C(lit.) |
| Physical Description | Other Solid[Merck Index] White powder[Alfa Aesar MSDS] |
| Dissociation Constants | 4.51 (at 25 °C) |
| Collision Cross Section | 129.29 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]130.9 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]134.7 Ų [M-2H+Na]- |
| Density | 1,329 g/cm3 |
| Refractive index | 1.4352 (estimate) |
| Flash point | 212°C/10mm |
| Storage conditions | Store below +30°C. |
| Physical state | Powder |
| pKa (acidity coefficient) | 4.71(at 25℃) |
| Color | White to slightly beige |
| pH | 3.77(1 mM solution)3.25(10 mM solution)2.74(100 mM solution) |
| Merck | 14,7431 |
| BRN | 1210024 |
| Henry's law constant | 2.6×107 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Stability | Stable. Incompatible with oxidizing agents, bases. Combustible. |
| Cosmetics Ingredients Functions | PLASTICISER |
| InChI | 1S/C7H12O4/c8-6(9)4-2-1-3-5-7(10)11/h1-5H2,(H,8,9)(H,10,11) |
| InChIKey | WLJVNTCWHIRURA-UHFFFAOYSA-N |
| SMILES | OC(=O)CCCCCC(O)=O |
| LogP (partition coefficient) | 0.610 |
| CAS DataBase Reference | 111-16-0(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | BZQ96WX25F |
| NIST Chemistry Reference | Heptanedioic acid(111-16-0) |
| EPA Substance Registry System | Heptanedioic acid (111-16-0) |
| UNSPSC Code | 12352106 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H319-H335 |
| GHS precautionary statements | P261-P264-P271-P280-P304+P340+P312-P305+P351+P338 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-36 |
| Water hazard class (WGK) | 2 |
| RTECS number | TK3677000 |
| Hazard Note | Irritant |
| TSCA inventory status | TSCA listed |
| Customs code | 29171990 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Eye Irrit. 2STOT SE 3 |
| Toxicity | LD50 orally in Rabbit: 7000 mg/kg |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 3.9% (7 of 179) of reports.WarningH315 (27.9%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, 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 179 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Chemical: Heptanedioic acidHeptanedioic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Heptanedioic acid 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)Status: Active Update: 27-07-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23725Pimelic acid: Does not have an individual approval but may be used under an appropriate group standard |
| Other safety information | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| Hazards summary | A skin and strong eye irritant[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Skin Irrit. 2 (27.9%) |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 2 |
| TSCA inventory status | TSCA listed |
| RTECS number | TK3677000 |
| Customs code | 29171990 |
| Toxicity | LD50 orally in Rabbit: 7000 mg/kg |
| Risk statements (R) | 36/37/38 |
| Signal word | Warning |
Applications & Uses
Description
Pimelic acid is the organic compound with the formula HO2C(CH2)5CO2H which has been synthesized from cyclohexanone and from salicylic acid. In the former route, the additional carbon is supplied by dimethyloxalate, which reacts with the enolate.This acid (heptanedioic acid), from the Greek pimelh (pimele fat), as adipic acid, was isolated from oxidized fats. It was obtained in 1884 by Ganttner F et al. as a product of ricinoleic acid (hydroxylated oleic acid) from castor oil.
Uses
The major uses of pimelic acid are in plasticizers and polymers.
Uses
Pimelic Acid is a metabolite found in four biofluids from dairy cows that may be used as biomarkers of milk.