10030-85-0

Basic information

• Product Name: L(+)-Rhamnose monohydrate
• Synonyms: RHAMNOSE, L-(+)-;ISODULCIT;ISODULCIT MONOHYDRATE;L-RHA H2O;L-(+)-RHAMMNOSE MONOHYDRATE;L-(+)-RHAMNOPYRANOSE, MONOHYDRATE;L-(+)-RHAMNOSE;L-(+)-RHAMNOSE HYDRATE
• CAS NO: 10030-85-0
• Molecular Formula: C₆H₁₂O₅*H₂O
• Molecular Weight: 182.17
• EINECS: 222-793-4
• Product Categories: Carbohydrates;Carbohydrates & Derivatives;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;carbohydrate;Inhibitors
• Mol File: 10030-85-0.mol
• Article Data: 0

Chemical Properties

• Melting Point: 90-95 °C(lit.)
• Boiling Point: 323.9 °C at 760 mmHg
• Flash Point: 149.7 °C
• Appearance: White/Crystals or Crystalline Powder
• Density: 1.47
• Vapor Pressure: 1.99E-05mmHg at 25°C
• Refractive Index: 1.593
• Storage Temp.: Refrigerator
• Solubility: H2O: 0.1 g/mL, clear, colorless
• Water Solubility: 300 g/L (20 ºC)
• Stability: Stable at RT
• Merck: 14,8172
• BRN: 5988592
• CAS DataBase Reference: L(+)-Rhamnose monohydrate(CAS DataBase Reference)
• NIST Chemistry Reference: L(+)-Rhamnose monohydrate(10030-85-0)
• EPA Substance Registry System: L(+)-Rhamnose monohydrate(10030-85-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 24/25-37/39-26
• WGK Germany: 3
• F: 3
• TSCA: Yes
• Hazardous Substances Data: 10030-85-0(Hazardous Substances Data)

Usage

Description

L(+)-Rhamnose monohydrate, also known as L-Rhamnose, is a deoxy sugar that is naturally found in plants and bacteria. It plays a crucial role in maintaining the structure of plant cell walls and is a significant component of plant cell wall polysaccharides, such as rhamnogalacturonan I and rhamnogalacturonan II. Additionally, it is present in bacterial cell walls and serves as a major antigenic determinant, contributing to their pathogenicity. L(+)-Rhamnose monohydrate is non-absorbable in humans but is fermented by intestinal microbes. It appears as white crystals or a crystalline powder.

Uses

1. Used in the Food Industry:
L(+)-Rhamnose monohydrate is used as a starting material for the production of furanones, which are important compounds involved in the reaction of flavors developed during the preparation of various foods like bread, grilled meats, and other culinary delights. This application takes advantage of its role in flavor development, enhancing the taste and aroma of these products.
2. Used in the Pharmaceutical Industry:
L(+)-Rhamnose monohydrate has applications in cancer immunotherapies, where it is used as a monosaccharide conjugated to immunogens. This conjugation aids in the development of targeted therapies against cancer cells.
3. Used in the Biomedical Research:
Supplementation of L(+)-Rhamnose monohydrate has been shown to slow down gastric emptying, which can be beneficial in certain medical conditions and research studies.
4. Used in the Chemical Industry:
L(+)-Rhamnose monohydrate is also utilized as a component in the synthesis of various chemicals and compounds, particularly those related to the pharmaceutical and biotechnology sectors.

Biological Functions

L-Rhamnose is a part of plant cell wall polysaccharides, rhamnogalacturonan I and rhamnogalacturonan.It is also present in bacterial cell walland a major antigenic determinant contributing to its pathogenicity.L-rhamnose is non-absorbable in humans but is fermented by intestinal microbes. Supplementation of L-rhamnose slows down gastric emptying. L-rhamnose monosaccharide conjugated immunogens have applications in cancer immunotherapies. Intake of L-rhamnose elevates serum propionate levels. L-Rhamnose monohydrate has been used: in biofilm enhancement assay in S.pneumonia. as a sugar drink in humans undergoing intestinal barrier permeability test. for the standard curve generation in high performance liquid chromatography(HPLC).

Purification Methods

Crystallise the rhamnose from H2O or EtOH. It crystallises easily as the monohydrate by evaporating a solution in MeOH (90%) and H2O (10%). It is also purified by dissolving in a small volume of EtOH, adding a few drops of H2O and cooling. 1H NMR in D2O at 44o contains 60% -pyranose and 40% -pyranose forms [Angyal Adv Carbohydr Chem 42 15 1984.] [Smith J Chem Soc 1035 1940, McGeachin & Beevers Acta Cryst 10 227,230 197, Beilstein 1 IV 4261.]

InChI:InChI=1/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3-,4+,5+,6-/m0/s1

Synthetic route

1-Aminopiperidine (2213-43-6) + L-rhamnose monohydrate (10030-85-0) → (2S,3S,4S,5S)-1-(piperidin-1-ylimino)hexane-2,3,4,5-tetrol

Conditions	Yield
In methanol for 3.75h; Reflux;	83%

L-rhamnose monohydrate (10030-85-0) + N-aminopyrrolidine (16596-41-1) → (2S,3S,4S,5S)-1-(pyrrolidin-1-ylimino)hexane-2,3,4,5-tetrol

Conditions	Yield
In methanol for 2.5h; Reflux;	80%

1-azepanylamine (5906-35-4) + L-rhamnose monohydrate (10030-85-0) → (2S,3S,4S,5S)-1-(azepan-1-ylimino)hexane-2,3,4,5-tetrol

Conditions	Yield
In methanol for 3.25h; Reflux;	74%

L-rhamnose monohydrate (10030-85-0) → 6-deoxy-L-arabino-2-hexulose (14807-05-7)

Conditions	Yield
In pyridine for 5h; Heating;	63%

2-hexyldecan-1-ol (2425-77-6) + L-rhamnose monohydrate (10030-85-0) → 2-hexyldecyl 6-deoxy-L-mannopyranoside

Conditions	Yield
With sodium hydrogencarbonate In ethyl acetate	48%

L-rhamnose monohydrate (10030-85-0) → 6-deoxy-L-glucose (35867-45-9) + 6-deoxy-L-arabino-2-hexulose (14807-05-7) + 6-deoxy-L-ribo-hexulose (1026722-79-1)

Conditions	Yield
With pyridine for 5h; Product distribution; Heating; variation of time;	A 5% B 34% C 3%

2-octyldodecan-1-ol (5333-42-6) + L-rhamnose monohydrate (10030-85-0) → 2-octyldodecyl 6-deoxy-L-mannopyranoside

Conditions	Yield
	10%

2-decylteradecanol (58670-89-6) + L-rhamnose monohydrate (10030-85-0) → 2-decyltetradecyl 6-deoxy-L-mannopyranoside

Conditions	Yield
	6%

L-rhamnose monohydrate (10030-85-0) → 6-deoxy-L-fructose 2-nitrophenylhydrazone (72774-23-3, 72774-24-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 63 percent / pyridine / 5 h / Heating 2: H2O; ethanol / 0.17 h / Heating View Scheme

4-aminophenylacetic acid (1197-55-3) + L-rhamnose monohydrate (10030-85-0) → p-aminophenylacetic acid-N-L-rhamnoside

Conditions	Yield
With ammonium chloride In ethanol; nitrogen

3,6-diamino-10-methyl-acridine + L-rhamnose monohydrate (10030-85-0) → 3,6-Di-(α-L-rhamnopyranosyl-amino)-10-N-methylacridinium chloride (84208-01-5)

Conditions	Yield
With hydrogenchloride In water; ethyl acetate; acetone

proflavine hydrochloride (952-23-8) + L-rhamnose monohydrate (10030-85-0) → 3,6-Di-(α-L-rhamnopyranosyl-amino)-acridine (84207-95-4)

Conditions	Yield
In ethanol; water

L-rhamnose monohydrate (10030-85-0) → methyl 6-deoxy-α-L-mannopyranoside (14917-55-6)

Conditions	Yield
In methanol

Downstream Products

• 14917-55-6 methyl 6-deoxy-α-L-mannopyranoside 
• 72774-23-3 6-deoxy-L-fructose 2-nitrophenylhydrazone 
• 14807-05-7 6-deoxy-L-arabino-2-hexulose 
• 35867-45-9 6-deoxy-L-glucose 
• 1026722-79-1 6-deoxy-L-ribo-hexulose