beta-Cyclodextrin

HCID 444041
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Basic information

CAS
7585-39-9
Standard SMILES
OC[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@@H](O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@H]5[C@H](O)[C@@H](O)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@@H](O[C@H]7[C@H](O)[C@@H](O)[C@@H](O[C@H]8[C@H](O)[C@@H](O)[C@@H](O[C@H]1[C@H](O)[C@H]2O)O[C@@H]8CO)O[C@@H]7CO)O[C@@H]6CO)O[C@@H]5CO)O[C@@H]4CO)O[C@@H]3CO
InChIKey
WHGYBXFWUBPSRW-FOUAGVGXSA-N
Molecular formula
C42H70O35
Average molar mass
1,135 g/mol
Monoisotopic mass
1,134.36976394

Overview

Beta-cyclodextrin is a cyclodextrin composed of seven alpha-(14) linked D-glucopyranose units.

Names & identifiers

Preferred name
beta-Cyclodextrin
IUPAC
(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-5,10,15,20,25,30,35-heptakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecol
English name
β-Cyclodextrin
Molecular formula
C42H70O35
Molecular weight
1134.99

Names & synonyms

beta-CYCLODEXTRIN7585-39-9BetadexCycloheptaamyloseCyclomaltoheptaoseCycloheptaglucanCycloheptaglucosanKleptosebeta-Cycloamylosebeta-DextrinKleptose BRhodocap N
Show more names
β-CyclodextrinB-CyclodextrinCyclodextrinsBCDCARAWAYBETA BYCLODEXTRINBETA-CYCLODEXTRINE
Ringdex BRingdex BLbeta-CycloheptaamyloseBetacdOristar bcdRingdex-bBeta cyclodextrinDTXSID1020358

Database identifiers

CAS
7585-39-9
PubChem CID
444041
DTXSID
DTXSID1020358
ChEMBL
CHEMBL415690
ChEBI
CHEBI:495055
UNII
JV039JZZ3A
EC Number
231-493-2
Nikkaji
J245.583H

Properties

Computed structural properties

XLogP
-15
Topological polar surface area
554 Ų
Hydrogen bond donors
21
Hydrogen bond acceptors
35
Rotatable bonds
7
Heavy atoms
77

Experimental & physicochemical properties

PolymersBiological Agents -> Polysaccharides
CosmeticsChelating; Absorbent
Food AdditivesFLAVORING AGENT OR ADJUVANT, FORMULATION AID -> FDA Substance added to food
SolubilitySparingly soluble in water; freely soluble in hot water; slightly soluble in ethanol
Optical Rotation[α]D/25 + 160° to + 164° (1 % solution)
Physical Description · 3 items

Dry Powder

Virtually odourless white or almost white crystalline solid

White virtually odorless solid; [JECFA] White powder; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point
290 · 290-300 °C (dec.) (lit.)
Boiling point
844.96 °C · 844.96°C (rough estimate)
alpha
25 · [α]D25 +159～+165° (c=1, H2O) (After Drying)
Density
1.2296 · 1.2296 (rough estimate)
refractive index
1.75 · 1.7500 (estimate)
FEMA
4028 · 4028 | BETA-CYCLODEXTRIN

Safety & regulation

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 99.3% (151 of 152) of all reports.

Not Classified

Aggregated GHS information provided per 152 reports by companies from 3 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 5 items

Chemical: .beta.-Cyclodextrin

Regulation (EC) No 257/2010

.beta.-Cyclodextrin is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of .beta.-Cyclodextrin 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: 21-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/1942

Beta-cyclodextrin: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - .beta.-Cyclodextrin: Human health tier I assessment
Hazards Summary · 1 item

Composed of 7 glucose units joined together; Acceptable daily intake (ADI) of 0-5 mg/kg; [JECFA] Causes zonal hepatitis and acute tubular necrosis in 52-week constant oral studies of rats; Causes diffuse and zonal hepatitis in 7-week constant oral studies of rats; [RTECS] Causes mild skin and eye irritation in rabbits; Not a skin sensitizer in guinea pigs; [Sigma-Aldrich MSDS] See alpha-Cyclodextrin.

EPA Safer ChemicalChemical: Cyclodextrin
Hazard Classes and CategoriesNot Classified

Toxicology

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Toxicity DataLC50 (rat) > 4,900 mg/m3/4hr

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
2
tsca
TSCA listed
rtecs
GU2293000
hs_code
29400000
risk_code
36/37/38-20

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

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.

Compounds that bind to and reduce the biological availability of a chemical or pharmaceutical agent.

Uses & manufacturing

UsesPermitted for use as an inert ingredient in non-food pesticide products; [EPA] Used as flavoring agent and formulation aid; [FDA] Used as a thickening agent and an encapsulation agent for food additives, flavoring, and vitamins; [JECFA]
U.S. Production2023: 1,000,000 - <8,500,000 lb
Consumer UsesDeodorizer
Industry UsesDispersing agent
Use Classification · 6 items

EPA Safer Chemical Functional Use Classes -> Uncategorized

Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern

Food additives

Food Additives -> ADJUVANT -> JECFA Functional Classes

Food Additives -> ADJUVANT -> JECFA Functional Classes

Food Additives -> ADJUVANT -> JECFA Functional Classes

General Manufacturing Information · 2 items

All Other Chemical Product and Preparation Manufacturing

.beta.-Cyclodextrin: ACTIVE

Applications · 5 items

DescriptionCyclodextrins refer to a family of compounds consisting of sugar molecules bound together in ring (cyclic oligosaccharides). It is produced from starch through enzymatic conversion. Beta-cyclodextrin is the 7-membered sugar ring molecular form of cyclodextrin. Cyclodextrin has various applications. In the pharmaceutical industry, it can be used as complexing agents for increasing the solubility of poorly soluble drug as well as increasing their bioavailability and stability. It can also alleviate the gastrointestinal drug irritation, and prevent drug-drug and drug-excipient interactions. It can also be used in food, pharmaceutical, drug delivery, and chemical industries, as well as agriculture and environmental engineering.

OccurrenceA derivative of naturally occurring starch.

UsesUse to solubilize non-polar compounds such as fatty acids, lipids and cholesterol. Reported useful for the selective precipitation of enantiomeric, positional or structural isomersβ-Cyclodextrin is used with dansyl chloride to form water-soluble complexes for fluorescent labeling of proteins. It is an active ingredient of household odor eliminator. It is also used in personal care products like toothpastes, skin creams and dusting powders. It finds applications in the cosmetic industry for products like detergents and perfumes for the controlled release of fragrances. Further, it is used to produce HPLC columns allowing chiral enantiomers separation. In addition to this, it is used to decrease the level of cholesterol in milk fat.

Usesβ-Cyclodextrin is a cyclic oligosaccharide produced from starch via enzymatic conversion. β-Cyclodextrin is commonly used to produce HPLC columns allowing chiral enantiomers separation.

General DescriptionBeta-Cyclodextrin is the most abundant and cheap cyclic oligosaccharide that forms inclusion complexes with several drug molecules. Its main application is in tablet and capsule formulations.Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

Preparation methods

PreparationUsually produced commercially from Bacillus macerans or B. circulans fermentation of starch or starch hydrolysate.

Upstream & downstream products

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
山西锦洋药用辅料有限公司18234787927
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]

Additional notes

DefinitionChEBI: Beta-cyclodextrin is a cyclodextrin composed of seven alpha-(1->4) linked D-glucopyranose units.

Related reactions

70 records
New reaction record

Compound notes

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