488-38-0

Basic information

• Product Name: D-GLYCERO-D-TALO-HEPTITOL
• Synonyms: VOLEMITOL;D-GLYCERO-D-TALO-HEPTITOL;D-glycero-D-manno-heptitol;Nsc111937
• CAS NO: 488-38-0
• Molecular Formula: C7H16O7
• Molecular Weight: 212.2
• EINECS: 207-675-2
• Mol File: 488-38-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 558.3°Cat760mmHg
• Flash Point: 291.5°C
• Appearance: /
• Density: 1.549g/cm³
• Vapor Pressure: 3.03E-18mmHg at 25°C
• Refractive Index: 1.617
• CAS DataBase Reference: D-GLYCERO-D-TALO-HEPTITOL(CAS DataBase Reference)
• NIST Chemistry Reference: D-GLYCERO-D-TALO-HEPTITOL(488-38-0)
• EPA Substance Registry System: D-GLYCERO-D-TALO-HEPTITOL(488-38-0)

Safety Data

• Hazardous Substances Data: 488-38-0(Hazardous Substances Data)

Usage

Description

D-GLYCERO-D-TALO-HEPTITOL, also known as a heptitol, is a compound characterized by its heptane-1,2,3,4,5,6,7-heptol structure with R-configuration at positions 2, 3, 5, and 6. It is a versatile compound with various applications across different industries.

Uses

Used in Cryopreservation Industry:
D-GLYCERO-D-TALO-HEPTITOL is used as an additive for enhancing the cryopreservation of mammalian sperm. Its presence in the preservation medium improves the viability and motility of sperm cells during the freezing and thawing process, ultimately contributing to the success of artificial insemination and other assisted reproductive techniques.
(Note: The provided materials do not mention other industries or applications for D-GLYCERO-D-TALO-HEPTITOL. If there are additional uses in different industries, they can be listed following the format provided in the example.)

InChI:InChI=1/C7H16O7/c8-1-3(10)5(12)7(14)6(13)4(11)2-9/h3-14H,1-2H2/t3-,4-,5-,6-/m1/s1

Upstream product

• 3019-74-7 sedoheptulose 
• 3615-44-9 D-mannoheptulose 
• 1961-73-5 D-glycero-D-manno-heptose 
• 10589-31-8 D-glycero-D-altro-heptose 
• 13059-96-6 D-altro-[3]heptulose 
• 100816-37-3 hexa-O-acetyl-keto-D-altro-[2]heptulose 
• 1037290-51-9 tert-butyl (Z)-5,7-di-O-benzyl-2,3-dideoxy-D-ribo-hept-2-enoate 
• 1037290-81-5 5,7-di-O-benzyl-4,6-O-isopropylidene-D-glycero-D-manno-heptitol 
• 1037290-54-2 (Z)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-ribo-hept-2-enitol 
• 1037290-52-0 tert-butyl (Z)-5,7-di-O-benzyl-2,3-dideoxy-4,6-O-isopropylidene-D-ribo-hept-2-enoate 
• 5329-44-2 D-glycero-D-manno-heptonic acid-4-lactone 
• 132047-00-8 Methyl 2,3:4,5:6,7-Tri-O-isopropylidene-D-glycero-D-talo-heptonate 
• 105592-35-6 benzyl (Z)-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-hept-5-enofuranoside 
• 108182-77-0 methyl uronate 

Downstream Products

• 654-29-5 L-allo-1,3,4,5,6,7-Hexahydroxy-heptan-2-on 
• 6893-84-1 1,2,3,4,5,6,7-heptaacetoxy-heptane 
• 7143-52-4 O¹,O³;O⁴,O⁶;O⁵,O⁷-tribenzylidene-glycero-manno-heptitol 
• 5345-81-3 O³,O⁵-((s)-benzylidene)-D-glycero-D-gulo-heptitol 
• 4141-44-0 O¹,O³;O⁵,O⁷-((Ξ,Ξ)-dibenzylidene)-L-glycero-L-galacto-heptitol 
• 6893-84-1 D-glycero-D-gluco-heptitol hepta acetate 
• 6893-84-1 Hepta-O-acetyl-L-glycero-D-glucoheptit 
• 6893-84-1 meso-glycero-ido-heptitol acetate 
• 6893-84-1 Acetic acid (1R,2R,3S)-2,3,4-triacetoxy-1-((1S,2S)-1,2,3-triacetoxy-propyl)-butyl ester 
• 50-00-0 formaldehyd 
• 64-18-6 formic acid 
• 591-49-1 1-methylcyclohex-1-ene 
• 3624-30-4 L-gluco-[2]heptosulose-bis-phenylhydrazone 
• 654-29-5 DL-gluco-1,3,4,5,6,7-Hexahydroxy-heptan-2-on 

Relevant articles and documents

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Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol, a potent natural α-glucosidase inhibitor. Part 2

To examine the role of the side chain of kotalanol (2), a potent natural α-glucosidase inhibitor isolated from Salacia reticulata, on inhibitory activity, four diastereomers (11a-11d) with reversed configuration (S) at the C-4′ position in the side chain were synthesized and evaluated. Two of the four (11b and 11d) significantly lost their inhibitory activity against both maltase and sucrase, while the other two (11a and 11c) sustained the inhibitory activity to a considerable extent, showing distinct activity in response to the change of stereochemistry of the hydroxyls at the 5′and 6′ positions. Different activities were rationalized with reference to in silico docking studies on these inhibitors with hNtMGAM. Against isomaltase, all four analogs showed potent inhibitory activity as well as 2, and 11b and 11d exhibited enzyme selectivity.

Ascent of the Aldose Series by Four Carbon Atoms: Total Synthesis of D-glycero-D-talo-L-talo-Undecose Pentaacetonide

Enantiomerically pure undecose acetonide 9 was synthesized, through heptose intermediate 5, starting with D-glyceraldehyde acetonide (1).The key steps were two consecutive four-carbon homologations, each consisting of four reactions: (i) stereoselective elongation of the aldehyde precursor with 2-(trimethylsiloxy)furan, giving Cn+4 butenolide templates 2 and 6, (ii) anti-selective cis-dihydroxylation of the butenolide double bond, giving fully functionalized lactones 3 and 7, (iii) lactone ring opening and protection, giving open-chain methyl esters 4 and 8, and (iv) DIBAL reduction to aldoses 5 and 9.At the end of the eight-step sequence, undecose 9 was prepared in a 5.1percent overall yield, which corresponded to a 69.5percent average yield per step.