Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 18:05:05 UTC |
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Update Date | 2022-03-07 02:53:41 UTC |
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HMDB ID | HMDB0033369 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Hydroxypropyl methylcellulose |
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Description | Hydroxypropyl methylcellulose (HPMC or hypromellose) is a derivative of cellulose in which some of the hydroxyl groups in the repeating glucose units have been methoxylated or hydroxypropylated. HPMC is a thickening and binding agent approved for food use in the USA and the EU. As a food additive, HPMC is an emulsifier, thickening and suspending agent, and an alternative to animal gelatin. HPMC is used in deep fried batter. Its Codex Alimentarius code (E number) is E464. Since HPMC solution is a non-Newtonian solution and exhibits pseudoplastic behaviour (specifically, thixotropic behaviour) various test methods are available, and the results of different methods and viscometers do not necessarily correspond to each other. Due to viscometer acceptable ranges of error, the viscosity is typically given as a mean or as a range. The degree of substitution is the average level of methoxy substitution on the cellulose chain. Since there is a maximum of three possible sites of substitution with each cellulose molecule, this average value is a real number between 0 and 3. However, the degree of substitution is often expressed in percentages. Hypromellose (INN) is a semisynthetic, inert, viscoelastic polymer used as an ophthalmic lubricant, as well as an excipient and controlled-delivery component in oral medicaments, found in a variety of commercial products. Hypromellose is a solid and slightly off-white to beige powder and may be formed into granules. The compound forms colloids when dissolved in water. Although non-toxic, it is combustible and can react vigorously with oxidizing agents. Hypromellose solutions were patented as a semisynthetic substitute for tear-film. Its molecular structure is predicated upon a base celluloid compound that is highly water-soluble. Post-application, celluloid attributes of good water-solubility reportedly aid in visual clarity. When applied, a hypromellose solution acts to swell and absorb water, thereby expanding the thickness of the tear-film. Hypromellose augmentation therefore results in extended lubricant time presence on the cornea, which theoretically results in decreased eye irritation, especially in dry climates, home, or work environments. On a molecular level, this polymer contains beta-linked D-glucose units that remain metabolically intact for days to weeks. On a manufacturing note, since hypromellose is a vegetarian substitute for gelatin, it is slightly more expensive to produce due to semisynthetic manufacturing processes. Aside from its widespread commercial and retail availability over the counter in a variety of products, hypromellose 2% solution has been documented to be used during surgery to aid in corneal protection and during orbital surgery (Wikipedia ). |
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Structure | [H]OC[C@H]1O[C@@H](OC(C)O[H])[C@H](OC)[C@@H](OC(C)O[H])[C@@H]1O[C@@H]1O[C@H](COC)[C@@H](O[C@@H]2O[C@H](COC(C)O[H])[C@@H](O[H])[C@H](OC)[C@H]2O[H])[C@H](OC(C)O[H])[C@H]1O[H] InChI=1S/C29H54O20/c1-11(31)41-10-16-18(35)23(39-6)19(36)27(46-16)49-22-17(9-38-5)47-28(20(37)24(22)42-12(2)32)48-21-15(8-30)45-29(44-14(4)34)26(40-7)25(21)43-13(3)33/h11-37H,8-10H2,1-7H3/t11?,12?,13?,14?,15-,16-,17-,18-,19-,20-,21-,22-,23+,24-,25+,26-,27+,28+,29-/m1/s1 |
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Synonyms | Value | Source |
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e464 | HMDB | HPMC | HMDB | Hydroxypropyl methyl cellulose | HMDB | Hypromellose | HMDB | 2-Hydroxypropyl methyl cellulose | HMDB | 2-Hydroxypropyl methyl cellulose ether | HMDB | Cellulose, 2-hydroxypropyl methyl ether | HMDB | Cellulose hydroxypropyl methyl ether | HMDB | Hydroxypropyl methyl cellulose ether | HMDB |
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Chemical Formula | (C9H16O6)nC20H38O14 |
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Average Molecular Weight | Not Available |
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Monoisotopic Molecular Weight | Not Available |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 9004-65-3 |
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SMILES | [H]OC[C@H]1O[C@@H](OC(C)O[H])[C@H](OC)[C@@H](OC(C)O[H])[C@@H]1O[C@@H]1O[C@H](COC)[C@@H](O[C@@H]2O[C@H](COC(C)O[H])[C@@H](O[H])[C@H](OC)[C@H]2O[H])[C@H](OC(C)O[H])[C@H]1O[H] |
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InChI Identifier | InChI=1S/C29H54O20/c1-11(31)41-10-16-18(35)23(39-6)19(36)27(46-16)49-22-17(9-38-5)47-28(20(37)24(22)42-12(2)32)48-21-15(8-30)45-29(44-14(4)34)26(40-7)25(21)43-13(3)33/h11-37H,8-10H2,1-7H3/t11?,12?,13?,14?,15-,16-,17-,18-,19-,20-,21-,22-,23+,24-,25+,26-,27+,28+,29-/m1/s1 |
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InChI Key | VKXHPENDMSFNDF-LFNJRTATSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Oligosaccharides |
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Alternative Parents | |
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Substituents | - Oligosaccharide
- O-glycosyl compound
- Glycosyl compound
- Oxane
- Secondary alcohol
- Hemiacetal
- Oxacycle
- Organoheterocyclic compound
- Ether
- Dialkyl ether
- Acetal
- Hydrocarbon derivative
- Primary alcohol
- Alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 1000000 mg/L @ 25 °C (est) | The Good Scents Company Information System | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredictor | Adduct Type | CCS Value (Å2) | Reference |
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DeepCCS | [M+H]+ | 239.918 | 30932474 | DeepCCS | [M-H]- | 238.242 | 30932474 | DeepCCS | [M-2H]- | 272.274 | 30932474 | DeepCCS | [M+Na]+ | 246.075 | 30932474 |
Predicted Kovats Retention IndicesNot Available |
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| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxypropyl methylcellulose 10V, Positive-QTOF | splash10-0np1-0907056000-a20456a8c09062f2e0e8 | 2018-11-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxypropyl methylcellulose 20V, Positive-QTOF | splash10-002b-0904030000-a2fc428522b329eef9db | 2018-11-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxypropyl methylcellulose 40V, Positive-QTOF | splash10-002b-0902010000-bd5b2cd78a9e5db6f93d | 2018-11-27 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxypropyl methylcellulose 10V, Negative-QTOF | splash10-00di-3000028900-9af0144973cd0b692e77 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxypropyl methylcellulose 20V, Negative-QTOF | splash10-0cdi-9000014000-c1e8854cd7c384cc09d5 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxypropyl methylcellulose 40V, Negative-QTOF | splash10-01ox-9201212000-1dab383e8f37579f2a31 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxypropyl methylcellulose 10V, Positive-QTOF | splash10-00di-0020012900-f00e5198f18dd504fd67 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxypropyl methylcellulose 20V, Positive-QTOF | splash10-0kms-3491645500-cdd62ce79d0dd5163861 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxypropyl methylcellulose 40V, Positive-QTOF | splash10-0002-9513001000-ed60b3eb37527c52ce7d | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
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