inulin

Inulins are a group of naturally occurring polysaccharides produced by many types of plants, industrially most often extracted from chicory. Inulin is used by some plants as a means of storing energy and is typically found in roots or rhizomes. Most plants that synthesize and store inulin do not store other forms of carbohydrate such as starch.

Chemical data

Formula: C228H382O191
Molecular weight: 6179 g/mol
IUPAC name: (2R,3R,4S,5S,6R)-2-[(2S,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-2-[[(2R,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxymethyl]-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES: C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)CO)O)O)CO[C@]3([C@H]([C@@H]([C@H](O3)CO)O)O)CO[C@]4([C@H]([C@@H]([C@H](O4)CO)O)O)CO[C@]5([C@H]([C@@H]([C@H](O5)CO)O)O)CO[C@]6([C@H]([C@@H]([C@H](O6)CO)O)O)CO[C@]7([C@H]([C@@H]([C@H](O7)CO)O)O)CO[C@]8([C@H]([C@@H]([C@H](O8)CO)O)O)CO[C@]9([C@H]([C@@H]([C@H](O9)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO[C@]1([C@H]([C@@H]([C@H](O1)CO)O)O)CO)O)O)O)O
InChIKey: JYJIGFIDKWBXDU-MNNPPOADSA-N
XLogP: -70.2
Polar surface area: 3040 Å²
H-bond donors: 116
H-bond acceptors: 191
Formal charge: 0

via PubChem

Research

13,933 papers

Inulin: properties and health benefits.Food & function · 2023
Immunomodulatory effects of inulin and its intestinal metabolites.Frontiers in immunology · 2023
Inulin: Properties, health benefits and food applications.Carbohydrate polymers · 2016
Inulin: a multifaceted ingredient in pharmaceutical sciences.Journal of biomaterials science. Polymer edition · 2024
Engineered inulin-based hybrid biomaterials for augmented immunomodulatory responses.Carbohydrate polymers · 2024

via PubMed

Wikidata facts

Mass: 6176.01785464399

Show 3 more facts

chemical formula: C₂₂₈H₃₈₂O₁₉₁
isomeric SMILES: OC[C@H]1O[C@H](O[C@]2(CO[C@]3(CO[C@]4(CO[C@]5(CO[C@]6(CO[C@]7(CO[C@]8(CO[C@]9(CO[C@]%10(CO[C@]%11(CO[C@]%12(CO[C@]%13(CO[C@]%14(CO[C@]%15(CO[C@]%16(CO[C@]%17(CO[C@]%18(CO[C@]%19(CO[C@]%20(CO[C@]%21(CO[C@]%22(CO[C@]%23(CO[C@]%24(CO[C@]%25(CO[C@]%26(CO[C@]%27(CO[C@]%28(CO[C@]%29(CO[C@]%30(CO[C@]%31(CO[C@]%32(CO[C@]%33(CO[C@]%34(CO[C@]%35(CO[C@]%36(CO[C@]%37(CO[C@]%38(CO)O[C@H](CO)[C@@H](O)[C@@H]%38O)O[C@H](CO)[C@@H](O)[C@@H]%37O)O[C@H](CO)[C@@H](O)[C@@H]%36O)O[C@H](CO)[C@@H](O)[C@@H]%35O)O[C@H](CO)[C@@H](O)[C@@H]%34O)O[C@H](CO)[C@@H](O)[C@@H]%33O)O[C@H](CO)[C@@H](O)[C@@H]%32O)O[C@H](CO)[C@@H](O)[C@@H]%31O)O[C@H](CO)[C@@H](O)[C@@H]%30O)O[C@H](CO)[C@@H](O)[C@@H]%29O)O[C@H](CO)[C@@H](O)[C@@H]%28O)O[C@H](CO)[C@@H](O)[C@@H]%27O)O[C@H](CO)[C@@H](O)[C@@H]%26O)O[C@H](CO)[C@@H](O)[C@@H]%25O)O[C@H](CO)[C@@H](O)[C@@H]%24O)O[C@H](CO)[C@@H](O)[C@@H]%23O)O[C@H](CO)[C@@H](O)[C@@H]%22O)O[C@H](CO)[C@@H](O)[C@@H]%21O)O[C@H](CO)[C@@H](O)[C@@H]%20O)O[C@H](CO)[C@@H](O)[C@@H]%19O)O[C@H](CO)[C@@H](O)[C@@H]%18O)O[C@H](CO)[C@@H](O)[C@@H]%17O)O[C@H](CO)[C@@H](O)[C@@H]%16O)O[C@H](CO)[C@@H](O)[C@@H]%15O)O[C@H](CO)[C@@H](O)[C@@H]%14O)O[C@H](CO)[C@@H](O)[C@@H]%13O)O[C@H](CO)[C@@H](O)[C@@H]%12O)O[C@H](CO)[C@@H](O)[C@@H]%11O)O[C@H](CO)[C@@H](O)[C@@H]%10O)O[C@H](CO)[C@@H](O)[C@@H]9O)O[C@H](CO)[C@@H](O)[C@@H]8O)O[C@H](CO)[C@@H](O)[C@@H]7O)O[C@H](CO)[C@@H](O)[C@@H]6O)O[C@H](CO)[C@@H](O)[C@@H]5O)O[C@H](CO)[C@@H](O)[C@@H]4O)O[C@H](CO)[C@@H](O)[C@@H]3O)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O
canonical SMILES: OCC1OC(OC2(OC(CO)C(O)C2O)COC3(OC(CO)C(O)C3O)COC4(OC(CO)C(O)C4O)COC5(OC(CO)C(O)C5O)COC6(OC(CO)C(O)C6O)COC7(OC(CO)C(O)C7O)COC8(OC(CO)C(O)C8O)COC9(OC(CO)C(O)C9O)COC%10(OC(CO)C(O)C%10O)COC%11(OC(CO)C(O)C%11O)COC%12(OC(CO)C(O)C%12O)COC%13(OC(CO)C(O)C%13O)COC%14(OC(CO)C(O)C%14O)COC%15(OC(CO)C(O)C%15O)COC%16(OC(CO)C(O)C%16O)COC%17(OC(CO)C(O)C%17O)COC%18(OC(CO)C(O)C%18O)COC%19(OC(CO)C(O)C%19O)COC%20(OC(CO)C(O)C%20O)COC%21(OC(CO)C(O)C%21O)COC%22(OC(CO)C(O)C%22O)COC%23(OC(CO)C(O)C%23O)COC%24(OC(CO)C(O)C%24O)COC%25(OC(CO)C(O)C%25O)COC%26(OC(CO)C(O)C%26O)COC%27(OC(CO)C(O)C%27O)COC%28(OC(CO)C(O)C%28O)COC%29(OC(CO)C(O)C%29O)COC%30(OC(CO)C(O)C%30O)COC%31(OC(CO)C(O)C%31O)COC%32(OC(CO)C(O)C%32O)COC%33(OC(CO)C(O)C%33O)COC%34(OC(CO)C(O)C%34O)COC%35(OC(CO)C(O)C%35O)COC%36(OC(CO)C(O)C%36O)COC%37(OC(CO)C(O)C%37O)COC%38(OC(CO)C(O)C%38O)CO)C(O)C(O)C1O

Sources (4)

via Wikidata · CC0

~13 min read

Article

13 sections

Contents

Origin and history
Chemical structure and properties
Uses
Harvesting and extraction
Processed foods
Medical
Possible side effects
Industrial use
Biochemistry
Calculation of glomerular filtration rate
Metabolism ''in vivo''
Natural sources
References

The inulins belong to a class of dietary fiber known as fructans. In 2018, the United States Food and Drug Administration approved inulin as a dietary fiber ingredient used to improve the nutritional value of manufactured food products. Using inulin to measure kidney function is the "gold standard" for comparison with other means of estimating glomerular filtration rate.