30738-01-3

Basic information

• Product Name: D-Apio-α-D-furanose
• Synonyms: D-Apio-α-D-furanose
• CAS NO: 30738-01-3
• Molecular Formula: C₅H₁₀O₅
• Molecular Weight: 150.1299
• Mol File: 30738-01-3.mol

Chemical Properties

• Boiling Point: 364.2±42.0 °C(Predicted)
• Appearance: /
• Density: 1.711±0.06 g/cm3(Predicted)
• PKA: 12.16±0.60(Predicted)
• CAS DataBase Reference: D-Apio-α-D-furanose(CAS DataBase Reference)
• NIST Chemistry Reference: D-Apio-α-D-furanose(30738-01-3)
• EPA Substance Registry System: D-Apio-α-D-furanose(30738-01-3)

Safety Data

• Hazardous Substances Data: 30738-01-3(Hazardous Substances Data)

Upstream product

• 70147-50-1 2,3-O-isopropylidene-β-D-apiofuranose 
• 1451183-90-6 benzyl 2-O-β-D-apiofuranosyl-(1→2)-β-D-glucopyranosylbenzoate 
• 1350889-91-6 (7S,8R)-9'-[β-D-apiofuranosyl-(1->6)-β-D-glucopyranosyloxy]-3,3'-dimethoxy-8,4'-oxyneolign-7'-ene-4,7,9-triol 
• 1351413-74-5 5,3',4'-trihydroxy-6,7-dimethoxy-8-C-[β-D-apiofuranosyl-(1->2)]-β-D-glucopyranosyl flavonoside 
• 1269988-75-1 quercetin 3-O-(3-O-methyl-α-L-rhamnopyranosyl)-(1->5)-O-β-D-apiofuranoside 
• 1011259-98-5 5''-O-trans-feruloyl-6'-O-β-D-apiofuranosylvanilloloside 
• 1011259-97-4 5''-O-trans-feruloyl-6'-O-β-D-apiofuranosylcalleryanin 
• 1011259-96-3 6'-O-β-D-apiofuranosylcalleryanin 

Downstream Products

• 6013-71-4 N-benzylphenylhydrazone of D-apiose 
• 10592-17-3 (3S)-2-hydroxymethylbutane-1,2,3,4-tetrol 

Relevant articles and documents

Chemical structures of constituents from the seeds of Cassia auriculata

Five new diterpene glycosides, auricuosides I (1), II (2), III (3), IV (4), and V (5), a new flavonol glycoside, auricuoflavonoside I (6), and a new megastigmane glycoside, auricuomegastigmane I (7), were isolated from the seeds of Cassia auriculata, together with 11 known constituents. The chemical structures of seven new constituents were characterized on the basis of chemical and physicochemical evidence. In the present study, auricuosides I (1)-V (5) were obtained from the seeds of C. auriculata. To the best of our knowledge, there is no report about the isolation of kaurenolides with hydroxy group at 14-position from plants. This finding is interesting from the perspective of chemotaxonomy and biosynthesis of kaurenolide.

The phenolic acids from Oplopanax elatus Nakai stems and their potential photo-damage prevention activity

25 phenolic acids, including four new isolates, eurylophenosides A–D (1–4) and 21 known ones (5–25) were isolated and identified from the stems of Oplopanax elatus Nakai. Among the known compounds 5–9, 11–13, 16, 18–25 were isolated from the genus for the first time; 17 was first obtained from the plant; and the NMR data of 22 was reported here first. Meanwhile, the UVB-induced photodamage model of HaCaT cells was used to study the prevent-photodamage abilities of compounds 1–2, 4–8, 11–13 and 15–25 with a nontoxic concentration at 50?μM. Moreover, a dose-dependent experiment was conducted for active compounds at the concentration of 10, 25, and 50?μM, respectively. Consequently, pretreatment with compounds 1, 16, 17, 19, 20, 22, 24 and 25 could suppress the cell viability decreasing induced by UVB irradiation in a concentration-dependent manner. These results indicated that phenolic acids were one kind of material basis with prevent-photodamage activity of O. elatus. Graphic abstract: [Figure not available: see fulltext.].

Bufadienolides and ecdysteroids from the whole plants of Helleborus niger and their cytotoxicity

A new bufadienolide (1), two new bufadienolide glycosides (2 and 3), a new ecdysteroid (4), and four known compounds (5–8), were isolated from the whole plants of Helleborus niger L. (Ranunculaceae). The structures of the new compounds (1–4) were determined by spectroscopic analysis, including 2D NMR spectral data, and hydrolytic studies. Compounds 1–6 showed cytotoxicity against HL-60 human leukemia cells, A549 human lung adenocarcinoma cells, and SBC-3 human small-cell lung cancer cells, with IC50 values ranging from 0.0055 to 1.9?μM. HL-60 cells treated with either 3 or 4 showed apoptosis characteristics, such as nuclear chromatin condensation, accumulation of sub-G1 cells, and activation of caspase-3/7.

Triterpenic saponins from Medicago marina L

The saponin composition of leaves and roots from Medicago marina L., sea medic, was investigated by a combination of chromatographic, spectroscopic and spectrometric (GC, LC, ESI-MS/MS, NMR) methods. Several compounds were detected and quantified by HPLC using the external standard method. Saponins from this plant species consist of a mixture of high molecular weight bidesmosidic derivatives of medicagenic and zanhic acid, containing up to six sugars in the molecules. Six of the detected saponins were previously isolated and reported as constituents of other Medicago spp.; one saponin was previously described in other plant species; four saponins are undescribed compounds in Medicago and never reported before in other plant species. These are: 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosylzanhic acid 28-O-β-D-xylopyranosyl-(1 → 4)-[β-D-apiofuranosyl-(1 → 3)]-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester; 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosylzanhic acid 28-O-β-D-xylopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester; 3-O-β-D-glucopyranosyl-(1 → 2)-β-D-glucopyranosylmedicagenic acid 28-O-β-D-xylopyranosyl-(1 → 4)-[α-L-arabinopyranosyl-(1 → 3)]-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester and 3-O-β-D-glucopyranosylmedicagenic acid 28-O-β-D-xylopyranosyl-(1 → 4)-[α-L-arabinopyranosyl-(1 → 3)]-α-L-rhamnopyranosyl-(1 → 2)-α-L-arabinopyranosyl ester. The specific saponins synthesized by M. marina may have a role in its tolerance to environment, representing a reservoir of osmolytic sugars.

Phytochemical Study of Stem and Leaf of Clausena lansium

Clausena lansium Lour. Skeels (Rutaceae) is widely distributed in South China and has historically been used as a traditional medicine in local healthcare systems. Although the characteristic components (carbazole alkaloids and coumarins) of C. lansium have been found to possess a wide variety of biological activities, little attention has been paid toward the other components of this plant. In the current study, phytochemical analysis of isolates from a water-soluble stem and leaf extract of C. lansium led to the identification of 12 compounds, including five aromatic glycosides, four sesquiterpene glycosides, two dihydrofuranocoumarin glycosides, and one adenosine. All compounds were isolated for the first time from the genus Clausena, including a new aromatic glycoside (1), a new dihydrofuranocoumarin glycoside (6), and two new sesquiterpene glycosides (8 and 9). The phytochemical structures of the isolates were elucidated using spectroscopic analyses including NMR and MS. The existence of these compounds demonstrates the taxonomic significance of C. lansium in the genus Clausena and suggests that some glycosides from this plant probably play a role in the anticancer activity of C. lansium to some extent.

Phenolic Constituents from Fallopia multiflora (Thunberg) Haraldson

Four naphtolic glycosides (1-4), three anthraquinones (5-7), two stilbenes (8-9), one benzyl glycoside (10), and one flavonoid (11) were isolated from the roots of Fallopia multiflora. The new compounds were elucidated to be 6-hydroxymusizin 8-O-α-D-apiof

Naphthalene glycosides in the Thai medicinal plant Diospyros mollis

This study evaluated methanol extracts from the leaves and branches of the Thai medicinal plant Diospyros mollis (Ebenaceae). Seven triterpenes and 22 aromatic compounds, including five new compounds, were isolated, and their structures were determined. The new compounds had the following structures: diospyrol glycoside (makluoside A, 1), 8,8′-di-O-6-β-d-apiofuranosyl-β-d-glucopyranosyl-6,6′-dimethyl-2,3′-binaphthalene-1-ol-1′,4′- dione (makluoside B, 2), and 3-methyl-1,8- naphthalenediol glycosides (makluosides C-E, 3–5). Makluoside B is the first example of a naphthoquinone glycoside that has both a 3-methyl-1,8-naphthalenediol unit and a 5-hydroxy-7-methyl-1,4-naphthoquinone unit. The hyaluronidase inhibitory activity of the isolates was evaluated, revealing that one of the triterpene derivatives possessed moderate inhibitory activity.

The antitumor constituents from hedyotis diffusa willd

As a TCM, Hedyotis diffusa Willd. has been using to treat malignant tumors, and many studies also showed that the extracts from Hedyotis diffusa Willd. possessed evident antitumor activities. Therefore, we carried out chemical study on Hedyotis diffusa Willd. and investigated the cytotoxicity of the obtained compounds on a panel of eight tumor cell lines. As a result, four new compounds were isolated from Hedyotis diffusa Willd., including three iridoid glycosides of Shecaoiridoidside A-C (1-3) and a cerebroside of shecaocerenoside A (4). Also, six known iridoid compounds (5-10) were also obtained. The cytotoxicity of all compounds against human tumor cell lines of HL-60, HeLa, HCT15, A459, HepG2, PC-3, CNE-2, and BCG-823 were also evaluated in vitro. New compound 3 exhibited evident cytotoxicity to all tumor cell lines except the Hela, and the IC50 values are from 9.6 μ M to 62.2 μ M, while new compound 4 showed moderate cytotoxicity to all the cell lines, and the IC50 values are from 33.6 μ M to 89.3 μ M. By contrast, new compound 1 and known compound 9 showed moderate cytotoxicity to HCT15, A459, and HepG2 selectively. Known compound 7 also exhibited moderate cytotoxicity to HCT15 and A459 selectively.

Cytotoxic steroidal saponins from Trillium kamtschaticum

Eight new steroidal saponins, trillikamtosides K–R (1–8), along with three known analogues, were isolated from the whole plants of Trillium kamtschaticum. Their structures were unambiguously established by interpretation of spectroscopic data (MS and NMR) and chemical methods. Compound 1 had a rare aglycone featuring a skeleton of 16-oxaandrost-5-en-3-ol-17-one, which was reported for the first time. The isolated saponins were tested for cytotoxicities against HCT116 cells, and trillikamtoside R (8) was found to show the most cytotoxic effect with an IC50 value of 4.92?μM.

From the stems of Hydrangea paniculata Sieb

known compounds (4, 5), have been isolated from the stems of Hydrangea paniculata Sieb. Their structures have been determined by spectroscopic and chemical methods. Furthermore, compound 1 (50 μM) exhibited significant hepatoprotective activity against N-