5328-37-0

Basic information

• Product Name: L-ARABINOSE
• Synonyms: L-(+)-Arbinose Vetec(TM) reagent grade, >=99%;X-GAL (SOLID POWDER;L-(+)-Arabinose Vetec(TM) reagent grade, >=99%;L-Arabinose Microbiological Grade≥ 99% (HPLC);L-ARA;FEMA 3255;PECTIN SUGAR;(3R,4S,5S)-2,3,4,5-tetrol--oxane
• CAS NO: 5328-37-0
• Molecular Formula: C₅H₁₀O₅
• Molecular Weight: 150.13
• EINECS: 226-214-6
• Product Categories: Food Additives;CARBOHYDRATE;Arabinose;Basic Sugars (Mono & Oligosaccharides);Biochemistry;Sugars;Biochemicals and Reagents;BioUltraBiochemicals and Reagents;Carbohydrate LibraryResearch Essentials;CarbohydrateMetabolomics;CarbohydratesCarbohydrates;Metabolic Pathways;Metabolites and Cofactors on the Metabolic Pathways Chart;Carbohydrates;Carbohydrates A to;Carbohydrates A-CBiochemicals and Reagents;Core Bioreagents;Metabolic Libraries;Monosaccharide;Specialty Synthesis;Carbohydrate Synthesis;Monosaccharides;MonosaccharideSpecialty Synthesis
• Mol File: 5328-37-0.mol
• Article Data: 274

Chemical Properties

• Melting Point: 160-163 °C(lit.)
• Boiling Point: 415.5ºC at 760mmHg
• Flash Point: 219.2ºC
• Appearance: white crystalline powder
• Density: 1.508g/cm3
• Vapor Pressure: 9.92E-06mmHg at 25°C
• Refractive Index: 104 ° (C=10, H2O)
• Storage Temp.: room temp
• Solubility: H2O: 1 M at 20 °C, clear, colorless
• PKA: 12.46±0.20(Predicted)
• Water Solubility: almost transparency
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,761
• BRN: 1723085
• CAS DataBase Reference: L-ARABINOSE(CAS DataBase Reference)
• NIST Chemistry Reference: L-ARABINOSE(5328-37-0)
• EPA Substance Registry System: L-ARABINOSE(5328-37-0)

Safety Data

• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 5328-37-0(Hazardous Substances Data)

Usage

Description

L-Arabinose is considered a rare sugar that can be found naturally within the structures of most fruits and vegetables. Due to its low caloric sweetening effects, arabinose is commonly used in nutritional supplements and prescription drugs. In addition to its sweetening effects, when reacted with amino acid blends, using the Maillard Reaction, arabinose is able to contribute to the production of savory and meaty flavors used within the food and flavor industry.L-Arabinose is commonly used in the Flavor Industry to produce meaty or cooked/roasted flavors.

Chemical Properties

Different sources of media describe the Chemical Properties of 5328-37-0 differently. You can refer to the following data:
1. L-Arabinose is a white crystalline powder, It is a rare type of C5-sugar that naturally occurs in the hemicelluloses structure of most fruits and vegetables. Its name is derived from gum Arabic, another well-known food ingredient. Humans have always consumed L-Arabinose both pure as well as part of the hemicelluloses structure. The highest concentrations of L-Arabinose in food as monosaccharide can be found in instant coffee, wine and sake.
2. Arabinose is widely distributed in nature including Acacia and Larix species as a complex polysaccharide.

Occurrence

For biosynthetic reasons, most saccharides are almost always more abundant in nature as the "D"-form, or structurally analogous to D-glyceraldehyde. However, L-arabinose is in fact more common than D-arabinose in nature and is found in nature as a component of biopolymers such as hemicellulose and pectin. L-Arabinose is widely distributed in nature including Acacia and Larix species as a complex polysaccharide.

Uses

Different sources of media describe the Uses of 5328-37-0 differently. You can refer to the following data:
1. The L-arabinose operon, also known as the araBAD operon, has been the subject of much biomolecular research. The operon directs the catabolism of arabinose in E. coli, and it is dynamically activated in the presence of arabinose and the absence of glucose. In synthetic biology, arabinose is often used as a one-way or reversible switch for protein expression under the Pbad promoter in E. coli. This on-switch can be negated by the presence of glucose or reversed off by the addition of glucose in the culture medium which is a form of catabolite repression. L-Arabinose is an arabinose isomer widely found in nature, while D-arabinose is less common. L-Arabinose is a constituent of many biopolymers that make up plant cell walls. This monosaccharide is often used in cell culture media, serving as a bacterial carbon source, and can be used to distinguish between bacteria based on their fermentation abilities. L-Arabinose, in the absence of glucose, induces transcription of the ara operon in E. coli that encodes L-arabinose catabolizing enzymes. It does this by binding to the AraC protein and activating the PBAD promoter. The PBAD promoter is used in plasmid vectors as a switch for protein expression that can be turned on by L-arabinose or turned off by addition of glucose.
2. L-Arabinose is used as a substrate to identify, differentiate and characterize pentose sugar isomerase(s). L-Arabinose is used in the bioproduction of L-ribose.

Definition

l-enantiomers occur naturally. lArabinose is common in vegetable gums, especially arabic.

Preparation

By partial hydrolysis of mesquite gum.

Application

L-Arabinose is used as a substrate to identify, differentiate and characterize pentose sugar isomerase(s). L-Arabinose is used in the bioproduction of L-ribose.L-(+)-Arabinose is a pentose sugar that occurs naturally in corn fiber gum and acacia gum.L-(+)-Arabinose is used as a key starting material in the total synthesis of (+)-ambruticin, zaragozic acid A, (?)-radicamine B and (+)-herbarumin I.

benefits

L-Arabinose can play an important role in the management of blood glucose and insulin levels related to sucrose intake. The addition of L-Arabinose to a sugar containing diet has the following direct benefits: 1) up to 60% reduction of the glucose peak level related to sucrose consumption, 2) up to 60% suppression of the insulin peak level related to sucrose consumption, and 3) a sustained release of glucose to the body over a longer period of time. A low glycemic diet may have benefits like reduction of heart disease, lowering of blood cholesterol, management of body weight and composition, and prevention of type 2 diabetes. A low insulinic diet may lead to lower fat storage and prevention of pre-diabetes incidence. Sustained glucose release over a longer period of time has advantages for athletes and other people that value a responsible and healthy diet.

Flammability and Explosibility

Notclassified

Biological Activity

L-Arabinose is the naturally occurring isomer and is a constituent of plant polysaccharides. Most bacteria contain an inducible arabinose operon that codes for a series of enzymes and transporters that allows L-arabinose to be used as the sole carbon source in microbial culture.

Biochem/physiol Actions

L-(+)-Arabinose is a naturally occurring pentose sugar that has been shown to decrease lipogenesis in rat models due to its ability to inhibit sucrase activity.

InChI:InChI=1/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3-,4+,5?/m0/s1

Synthetic route

ducheside B → 3-O-methylellagic acid (51768-38-8) + L-arabinose (5328-37-0)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 80℃; for 1h;	A 85% B n/a

3,3′,4′-tri-O-methylellagic acid 4-O-α-L-arabinofuranoside → L-arabinose (5328-37-0) + 3,3',4-tri-O-methylellagic acid (1617-49-8)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 80℃; for 1h;	A n/a B 88%

3-O-methylellagic acid 4-O-α-L-arabinofuranoside → 3-O-methylellagic acid (51768-38-8) + L-arabinose (5328-37-0)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 80℃; for 1h;	A 78% B n/a

C27H28O16 → L-arabinose (5328-37-0) + L-Rhamnose (3615-41-6) + 3,4′-O-dimethyl ellagic acid

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 80℃; for 1h;	A n/a B n/a C 88%

ellagic acid 3-O-α-L-rhamnopyranosyl-4′-O-α-L-arabinofuranoside → L-arabinose (5328-37-0) + L-Rhamnose (3615-41-6) + ellagic acid (476-66-4)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 80℃; for 1h;	A n/a B n/a C 77%

Ganoderma capense heteropolysaccharide GCPB-2, 1.03E5 Da → D-xylose (58-86-6) + L-arabinose (5328-37-0)

Conditions	Yield
With trifluoroacetic acid In water at 120℃; for 6h; Sealed tube;

4-O-(α-L-arabinopyranosyl) nervogenic acid lindelofidine ester → L-arabinose (5328-37-0)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; water at 90℃; for 4h;

4-O-(α-L-arabinopyranosyl) nervogenic acid laburnine ester → L-arabinose (5328-37-0)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; water at 90℃; for 4h;

3-[(3-hydroxy-3-methylbutyl)-4-O-(α-L-arabinopyranosyl)]-5-(3-methyl-2-butenyl) benzoate lindelofidine ester → L-arabinose (5328-37-0)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; water at 90℃; for 4h;

(12R,20S,23S,24R)-20,25-dihydroxy-23,24-epoxy-12-O-α-L-arabinopyranosyl-3,4-secodammara-4(28)-en-3-oic acid → L-arabinose (5328-37-0)

Conditions	Yield
With hydrogenchloride In water at 100℃; for 3h;

(23E)-(20S)-(3α,12β)-20-hydroxy-dammara-23,25-dien-12-O-α-L-arabinopyranoside-3-O-α-L-arabinopyranoside → L-arabinose (5328-37-0)

Conditions	Yield
With hydrogenchloride In water at 100℃; for 3h;

3α-[(α-L-arabinopyranosyl)-oxy]-24(S),25-dihydroxy-30-oxo-lanost-8-ene → L-arabinose (5328-37-0)

Conditions	Yield
With hydrogenchloride In water at 80℃; for 6h;

4-O-[β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl] nervogenic acid lindelofidine ester → L-arabinose (5328-37-0) + D-glucose (50-99-7)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; water at 90℃; for 4h;

phyllaemblicins H4 → L-arabinose (5328-37-0) + D-glucose (50-99-7)

Conditions	Yield
With hydrogenchloride In water at 80℃; for 6h; Sealed tube;

3-O-α-L-arabinopyranosyl-phytolaccagenin-28-O-β-D-glucopyranosyl ester → L-arabinose (5328-37-0) + D-glucose (50-99-7)

Conditions	Yield
With potassium hydroxide In water for 2h; Reflux;
With hydrogenchloride In water at 90℃; for 3h;

trilliumoside A → L-arabinose (5328-37-0) + L-Rhamnose (3615-41-6)

Conditions	Yield
With trifluoroacetic acid In 1,4-dioxane; water at 90℃; for 3h;

trilliumoside B → L-arabinose (5328-37-0) + L-Rhamnose (3615-41-6)

Conditions	Yield
With trifluoroacetic acid In 1,4-dioxane; water at 90℃; for 3h;

trilliumoside C → L-arabinose (5328-37-0) + L-Rhamnose (3615-41-6)

Conditions	Yield
With trifluoroacetic acid In 1,4-dioxane; water at 90℃; for 3h;

trilliumoside D → L-arabinose (5328-37-0) + L-Rhamnose (3615-41-6)

Conditions	Yield
With trifluoroacetic acid In 1,4-dioxane; water at 90℃; for 3h;

trilliumoside E → L-arabinose (5328-37-0) + L-Rhamnose (3615-41-6)

Conditions	Yield
With trifluoroacetic acid In 1,4-dioxane; water at 90℃; for 3h;

trilliumoside F → L-arabinose (5328-37-0) + L-Rhamnose (3615-41-6)

Conditions	Yield
With trifluoroacetic acid In 1,4-dioxane; water at 90℃; for 3h;

trilliumoside G → L-arabinose (5328-37-0) + L-Rhamnose (3615-41-6)

Conditions	Yield
With trifluoroacetic acid In 1,4-dioxane; water at 90℃; for 3h;

trilliumoside H → L-arabinose (5328-37-0) + L-Rhamnose (3615-41-6)

Conditions	Yield
With trifluoroacetic acid In 1,4-dioxane; water at 90℃; for 3h;

(20S)-(3α,12β)-20-hydroxy-dammara-24-dien-12-O-β-D-quinovopyranoside-3-O-α-L-arabinopyranoside → L-arabinose (5328-37-0) + D-quionovose (7658-08-4)

Conditions	Yield
With hydrogenchloride In water at 100℃; for 3h;

3α-[(α-L-rhamnopyranosyl)-oxy]-24(S)-[(α-L-arabinopyranosyl)-oxy]-25-hydroxylanost-8-en-30-oic acid → L-arabinose (5328-37-0) + L-Rhamnose (3615-41-6)

Conditions	Yield
With hydrogenchloride In water at 80℃; for 6h;

(3S,12R,17R,20S,21S)-3-O-[β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl]-12-hydroxy-19-oxo-18,19-secours-13(18)-en-28,21-lactone → L-arabinose (5328-37-0) + D-glucose (50-99-7)

Conditions	Yield
Stage #1: (3S,12R,17R,20S,21S)-3-O-[β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl]-12-hydroxy-19-oxo-18,19-secours-13(18)-en-28,21-lactone With trifluoroacetic acid at 120℃; for 1.5h; Stage #2: With (S)-1-amino-2-propanol; sodium cyanoborohydride; acetic acid In methanol at 65℃; for 1.5h; Stage #3: With pyridine; acetic anhydride at 100℃; for 0.75h;

(3S,12R,17R,19S,20S,21S)-3-O-[β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl]-12,19-dihydroxy-18,19-secours-13(18)-en-28,21-lactone → L-arabinose (5328-37-0) + D-glucose (50-99-7)

Conditions	Yield
Stage #1: (3S,12R,17R,19S,20S,21S)-3-O-[β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl]-12,19-dihydroxy-18,19-secours-13(18)-en-28,21-lactone With trifluoroacetic acid at 120℃; for 1.5h; Stage #2: With (S)-1-amino-2-propanol; sodium cyanoborohydride; acetic acid In methanol at 65℃; for 1.5h; Stage #3: With pyridine; acetic anhydride at 100℃; for 0.75h;

3β-O-[β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl]-19α-hydroxy-olean-12-en-28-oic acid → L-arabinose (5328-37-0) + D-glucose (50-99-7)

Conditions	Yield
Stage #1: 3β-O-[β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl]-19α-hydroxy-olean-12-en-28-oic acid With trifluoroacetic acid at 120℃; for 1.5h; Stage #2: With (S)-1-amino-2-propanol; sodium cyanoborohydride; acetic acid In methanol at 65℃; for 1.5h; Stage #3: With pyridine; acetic anhydride at 100℃; for 0.75h;

coreoside B → L-arabinose (5328-37-0) + D-glucose (50-99-7) + C14H18O3

Conditions	Yield
With hydrogenchloride; water In methanol at 85℃; for 15h;

3-O-α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin → D-xylose (58-86-6) + L-arabinose (5328-37-0) + L-Rhamnose (3615-41-6)

Conditions	Yield
With hydrogenchloride In water at 90℃; for 6h;

L-arabinose (5328-37-0) + acetic anhydride (108-24-7) → 2,3,4,5-tetra-O-acetyl-L-arabinose (5139-19-5)

Conditions	Yield
In pyridine at 50℃; for 10h; Acetylation;	100%
With pyridine; N-Bromosuccinimide; hydrogen cation; ethanethiol Multistep reaction;

L-arabinose (5328-37-0) → L-arabinonitrile

Conditions	Yield
With phenoxyamine hydrochloride In aq. phosphate buffer; water-d2 at 20℃; for 12h;	100%

L-arabinose (5328-37-0) + 1,1-dimethylhydrazine (57-14-7) → (2S,3R,4S,E)-5-(2,2-dimethylhydrazono)pentane-1,2,3,4-tetraol

Conditions	Yield
With Amberlyst 15 In methanol at 20℃; for 24h;	99%

L-arabinose (5328-37-0) + ethanethiol (75-08-1) → L-arabinose di(ethylthio)acetal (43179-48-2)

Conditions	Yield
With dimethylbromosulphonium bromide at 0 - 5℃; for 0.416667h; neat (no solvent);	96%
Stage #1: ethanethiol With hydrogenchloride In water at 0℃; Stage #2: L-arabinose In water for 1h;	92%
In hydrogenchloride at 0℃; for 0.5h;	91%

L-arabinose (5328-37-0) → L-xylulose 1-phosphate (2547-08-2)

Conditions	Yield
With Thermotoga maritima MSB8 L-rhamnulose kinase; Bacillus subtilis L-arabinose isomerase; Pseudomonas Sp, ST-24 D-tagatose 3-epimerase; ATP; sodium hydroxide pH=7.5; Enzymatic reaction;	96%
With Pseudomonas Sp. St-24 D-tagatose 3-epimerase; Thermotoga maritima MSB8 L-arabinose isomerase; Thermotoga maritima MSB8 L-rhamnulose kinase; magnesium(II); manganese(II); ATP at 45℃; pH=Ca. 7.5; Enzymatic reaction;

L-arabinose (5328-37-0) + naphthalene-1,8-diamine (479-27-6) → (1S,2R,3S)-1-(2,3-Dihydro-1H-perimidin-2-yl)-butane-1,2,3,4-tetraol (73858-38-5)

Conditions	Yield
In ethanol; water; acetic acid for 2h; Heating;	95%

L-arabinose (5328-37-0) + Trimethylenediamine (109-76-2) → hexahydro-2-(L-arabino-1,2,3,4-tetrahydroxybutyl)pyrimidine

Conditions	Yield
for 69h; Cyclization;	95%

L-arabinose (5328-37-0) + acetone (67-64-1) → 1,2;3,4-di-O-isopropylidene-β-L-arabinopyranose (27820-98-0)

Conditions	Yield
With sulfonated polystyrene cation exchange resin CAT600 at 40℃; for 3h; Green chemistry;	95%
With malonic acid; choline chloride for 0.333333h; Reflux; Green chemistry;	92%

L-arabinose (5328-37-0) + thiophenol (108-98-5) → (2S,3S,4R)-5,5-bis(phenylthio)pentane-1,2,3,4-tetraol (28697-82-7)

Conditions	Yield
With trifluoroacetic acid In water at 50 - 60℃; for 12h;	95%

L-arabinose (5328-37-0) + 6-hydrazino-1,3-dimethyl-1H-pyrimidine-2,4-dione (123506-40-1) → 1,3-Dimethyl-6-{N'-[(2S,3R,4S)-2,3,4,5-tetrahydroxy-pent-(Z)-ylidene]-hydrazino}-1H-pyrimidine-2,4-dione (69471-91-6)

Conditions	Yield
In methanol for 5h; Heating;	93%

6-(hydrazinocarbonylmethyl)-6H-indolo[2,3-b]quinoxaline (116989-58-3) + L-arabinose (5328-37-0) → L-arabinose (6-indolo[2,3-b]quinoxalin-6-yl)acetylhydrazone

Conditions	Yield
With acetic acid In ethanol; water for 0.2h; microwave irradiation;	93%

L-arabinose (5328-37-0) + (2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetic acid hydrazide (5358-18-9) → C11H16N4O7

Conditions	Yield
With acetic acid In ethanol; water for 5h; Heating;	93%

L-arabinose (5328-37-0) + N-aminopyrrolidine (16596-41-1) → (2S,3R,4S)-5-(pyrrolidin-1-ylimino)pentane-1,2,3,4-tetrol

Conditions	Yield
In methanol for 3h; Reflux;	93%

L-arabinose (5328-37-0) → L-ribulose 1-phosphate

Conditions	Yield
With Bacillus subtilis L-arabinose isomerase; human fructosekinase; ATP; sodium hydroxide pH=7.5; Enzymatic reaction;	93%
With Human fructokinase; Thermotoga maritima MSB8 L-arabinose isomerase; magnesium(II); manganese(II); ATP at 37℃; pH=Ca. 7.5; Enzymatic reaction;

2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetohydrazide (1000071-56-6) + L-arabinose (5328-37-0) → C12H18N4O7

Conditions	Yield
With acetic acid In ethanol; water for 5h; Heating;	92%

L-arabinose (5328-37-0) → D-ribulose 5-phosphate

Conditions	Yield
With Bacillus subtilis L-arabinose isomerase; L-ribulose kinase; ATP; sodium hydroxide pH=7.5; Enzymatic reaction;	92%

1-thiopropane (107-03-9) + L-arabinose (5328-37-0) → L-arabinose dipropyl dithioacetal (121471-02-1)

Conditions	Yield
With dimethylbromosulphonium bromide at 0 - 5℃; for 0.666667h; neat (no solvent);	91%
With hydrogenchloride

L-arabinose (5328-37-0) + N-Methyl-N-(4-phenyl-thiazol-2-yl)hydrazin (67399-25-1) → L-Arabinose-N-methyl-N-(4-phenyl-thiazol-2-yl)hydrazon (120191-88-0)

Conditions	Yield
In ethanol; acetic acid for 24h; Ambient temperature;	91%

L-arabinose (5328-37-0) + N-Methyl-N-(4-phenyl-thiazol-2-yl)hydrazin (67399-25-1) → (2S,3R,4S)-5-[Methyl-(4-phenyl-thiazol-2-yl)-hydrazono]-pentane-1,2,3,4-tetraol

Conditions	Yield
In ethanol; acetic acid for 24h; Ambient temperature;	91%

L-arabinose (5328-37-0) + N-Methyl-N-<4-(p-chlor-phenyl)-thiazol-2-yl>hydrazin (112357-63-8) → (2S,3R,4S)-5-{[4-(4-Chloro-phenyl)-thiazol-2-yl]-methyl-hydrazono}-pentane-1,2,3,4-tetraol

Conditions	Yield
In ethanol; acetic acid for 24h; Ambient temperature;	91%

L-arabinose (5328-37-0) + benzoyl chloride (98-88-4) → 1,2,3,4-tetra-O-benzoyl-β-L-arabinopyranose (7473-44-1) + 1,2,3,5-tetra-O-benzoyl-α-L-arabinofuranose (202415-33-6)

Conditions	Yield
With pyridine; dmap at 25℃;	A 91% B 1%

L-arabinose (5328-37-0) + benzoyl chloride (98-88-4) → 1,2,3,4-tetra-O-benzoyl-β-L-arabinopyranose (7473-44-1)

Conditions	Yield
With pyridine; dmap at 20℃;	90%
With pyridine

L-arabinose (5328-37-0) + N-Methyl-N-<4-(p-brom-phenyl)-thiazol-2-yl>hydrazin (112357-62-7) → (2S,3R,4S)-5-{[4-(4-Bromo-phenyl)-thiazol-2-yl]-methyl-hydrazono}-pentane-1,2,3,4-tetraol

Conditions	Yield
In ethanol; acetic acid for 24h; Ambient temperature;	90%

L-arabinose (5328-37-0) + phenylmethanethiol (100-53-8) → L-arabinose dibenzyl dithioacetal (40733-11-7)

Conditions	Yield
With hydrogenchloride	88%
With hydrogenchloride for 0.5h;	87%
With hydrogenchloride

L-arabinose (5328-37-0) + benzoyl chloride (98-88-4) → 1',2',3',4'-tetra-O-benzoyl-α/β-L-arabinopyranose (212499-83-7)

Conditions	Yield
In pyridine; dichloromethane at 20℃;	88%

(N4-acetylcytosin-1-yl)acetohydrazine (1041404-16-3) + L-arabinose (5328-37-0) → L-(+)-arabinose 2-[4-acetamido-2-oxopyrimidin-1(2H)-yl]acetylhydrazone

Conditions	Yield
With acetic acid In ethanol; water Heating;	88%

L-arabinose (5328-37-0) + (5,6-diphenyl-[1,2,4]triazin-3-yl)-hydrazine (21383-24-4) → (2S,3R,4S)-5-[(5,6-Diphenyl-[1,2,4]triazin-3-yl)-hydrazono]-pentane-1,2,3,4-tetraol

Conditions	Yield
In methanol; water for 0.333333h; Heating;	87%

L-arabinose (5328-37-0) + 2-hydrazineyl-6-phenylpyrimidin-4(3H)-one (86799-26-0) → 6-Phenyl-2-{N'-[(2S,3R,4S)-2,3,4,5-tetrahydroxy-pent-(E)-ylidene]-hydrazino}-3H-pyrimidin-4-one

Conditions	Yield
In ethanol; water for 0.25h; Condensation; Heating;	87%

Upstream product

• 685-73-4 D-galacturonic acid 
• 6798-48-7 (2R,3S,4S)-4-Hydroxy-2,3,5-trimethoxy-pentanal 
• 449173-64-2 methyl α,β-L-arabinopyranoside 
• 114906-74-0 (3β)-O-6-deoxy-α-L-mannopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-β-Dglucopyranosyl ester 3-(α-L-arabinopyranosyloxy)olean-12-en-28-oic acid 
• 114912-35-5 ciwujianoside D₁ 
• 114892-57-8 ciwujianoside D₂ 
• 114902-16-8 yemuoside YM₁₀ 
• 114906-75-1 ciwujianoside C₄ 
• 114892-56-7 ciwujianoside C₂ 
• 7647-01-0 hydrogenchloride 
• 51885-64-4 1,2-O-isopropylidene-β-L-arabinofuranose 
• 64-18-6 formic acid 
• 110-82-7 cyclohexane 
• 72520-92-4 paeonolide 

Downstream Products

• 75241-37-1 (1R)-1-piperidino-1,5-anhydro-L-arabitol 
• 64-18-6 formic acid 
• 20235-19-2 arabinose 
• 79-33-4 L-Lactic acid 
• 4460-61-1 L-Arabinose-diisobutyldithioacetal 
• 109410-36-8 1-(3-methyl-4-ethyl-anilino)-1-deoxy-L-arabitol 
• 903637-88-7 4,5-Bis-(phenyl-hydrazono)-pentane-1,2,3-triol 
• 288-32-4 1H-imidazole 
• 98-01-1 furfural 

Relevant articles and documents

Antiacetylcholinesterase triterpenes from the fruits of: Cimicifuga yunnanensis

Two new cycloartane triterpenes, cimyunnin E (1), containing a unique oxaspiro[4.4]nonanedione moiety based on rings D and E, together with cimicifine B (2), a 25,26,27-trinortriterpene featuring a pyridine ring E, were purified from the fruits of Cimicifuga yunnanensis. Their structures were elucidated by spectroscopic methods and ECD (electronic circular dichroism calculations). Compounds 1 and 2 showed significant acetylcholinesterase (AChE) inhibition with IC50 values of 1.58 and 3.87 μM, respectively. In addition, they noticeably enhanced the neurite outgrowth of nerve growth factor (NGF) mediated PC12 cells at a concentration of 10 μM.

Exceptionally high yields of furfural from assorted raw biomass over solid acids

Development of stable and recyclable solid acid catalysts in the efficient valorisation of hemicellulose to yield C5 sugars and furfural is vital to boost the prospects of using lignocelluloses for chemicals synthesis. Using an silicoaluminopho

Triterpenes from the aerial parts of Cimicifuga yunnanensis and their antiproliferative effects on p53N236S mouse embryonic fibroblasts

Nine new triterpene derivatives, yunnanterpenes A-F (1-6), 15,16-seco-cimiterpenes A and B (7, 8), and cimilactone C (9), and 15 known analogues (10-24) were isolated from the aerial parts of Cimicifuga yunnanensis. The new structures were established using a combination of MS, NMR, and single-crystal X-ray diffraction techniques. WT MEFs (wild-type mouse embryonic fibroblasts) and tumorigenic cell lines p53-/-+H-RasV12 and p53 -/-+p53N236S+H-RasV12 were used for evaluating active structures, targeting p53N236S (corresponding to p53N239S in humans) mutation. Compound 5 showed nonselective activities against these cell lines, with IC50 values of 5.8, 8.6, and 6.0 μM, respectively. Compound 4 exhibited greater selectivity against the p53 -/-+p53N236S+H-RasV12 cells (IC50 5.5 μM) than against the WT MEFs cells (IC50 14.3 μM).

Bruceadysentoside A, a new pregnane glycoside and others secondary metabolites with cytotoxic activity from brucea antidysenterica J. F. Mill. (simaroubaceae)

The chemical investigation of the root barks leaves and stem barks of Brucea antidysenterica J. F. Mill. (Simaroubaceae) led to the isolation of a new pregnane glycoside, named Bruceadysentoside A or 3-O-β-L-arabinopyranosyl-pregn-5-en-20-one (1) together with seventeen known compounds. Their structures were established from spectral data, mainly HRESIMS, 1D and 2D NMR and by comparison with literature data. Compounds 1, 2, 5, 6, 8, 10, 12 and 13 were tested in vitro for their effects on the viability of two different human cancer cell lines, namely prostate PC-3 adenocarcinoma cells and colorectal HT-29 adenocarcinoma cells. No substantial activities were recorded for 2, 10, 12 and 13 (up to 10 μM concentration). 1, 5 and 8 did not show strong anti-proliferative effects up to 100 μM, however, 6 exhibited a stronger anti-proliferative effect with IC50 values of ～ 100 μM against PC-3 and ～ 200 μM against HT-29.

POLYSACCHARIDES FROM THE INFLORESCENCES OF Matricaria matricarioides

Fractionation of the polysaccharide complex of the inflorescences of pineapple weed has given a galacturonan and a pectic acid.The structures of the galacturonan and pectic acid have been studied by the methods of enzymatic hydrolysis, periodate oxidation, and exhaustive methylation.It has been established that the galacturonan is a linear polysaccharide consisting of D-galacturonic acid residues in the pyranose form with α-1->4-bonds.The main polysaccharide chain of the pectic acid consists of D-galacturonic acid residues in the pyranose form, D-galactose, L-arabinose, and D-xylose residues are covalently bound to carbon atoms 2 or 3 of the main chain of the polysaccharide.

MK800-62F1, a new inhibitor of apoptotic cell death, from Streptomyces diastatochromogenes MK800-62F1. II. Structure elucidation

A new compound, MK800-62F1, was isolated from a cultured broth of Streptomyces diastatochromogenes MK800-62F1. The structure was determined by NMR analysis and degradation experiments.

Two new triterpenoid saponins: telephiifoliosides A and B from the roots of Corrigiola litoralis subsp. telephiifolia (Pourr.) Briq

The polar fraction of the MeOH extract of the roots of Corrigiola litoralis subsp. telephiifolia (Pourr.) Briq. (Caryophyllaceae) was investigated for its constituents and two previously unreported monodesmosides triterpene saponins, telephiifoliosides A and B (1 and 2), along with the known bonushenricoside A (3) were isolated. Their structures were elucidated by combined spectroscopic and spectrometric techniques (1H NMR, 13C NMR, HSQC, 1H-1H COSY, HMBC, TOCSY, NOESY, HRESIMS) and chemical methods. The structures of the new saponins were established as; 3-O-α-L-arabinopyranosyljaligonic acid (1), and 3-O-α-L-arabinopyranosylphytolaccagenin ester (2). Upon evaluation of the antiproliferative activity on human malignant epithelial (HeLa) cells, none of the isolated compounds was efficient at the concentration of 33 μM. Highlights This is the first phytochemical study on Corrigiola litoralis subsp. telephiifolia. Two new saponins were isolated from the roots of Corrigiola litoralis subsp. telephiifolia. The isolated compounds were tested for their antiproliferative activity.

New lupane-type and ursane-type triterpene saponins from the leaves of Trevesia palmata

Three new triterpene saponins including two lupane-types and an ursane-type were isolated from the leaves of Trevesia palmata. Their structures were determined as 2α,3β,23-trihydroxylup-20(29)-en-28-oic acid 3-O-α-L-arabinopyranoside (1), 2α,3β,23-trihydroxylup-20(29)-en-28-oic acid 3-O-[α-L-arabinopyranoside]-28-O-[β-D-glucopyranosyl] ester (2), and 2α,3β,23-trihydroxyurs-12-en-28-oic acid 3-O-[α-L-arabinopyranoside]-28-O-[β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl] ester (3) by analysis of their HR-ESI-MS, 1D and 2D NMR spectra. The 2α,3β,23-trioxygenated pentacyclic triterpenes were uncommonly found in the nature. At concentration of 100 μM, compounds 1–3 inhibited NO production in LPS activated BV2 cells with inhibitory rates of 17.4 ± 1.8%, 33.1 ± 1.2%, and 11.7 ± 2.2%, respectively. But, they did not significantly inhibit yeast α-glucosidase activity.