(2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal

Base Information

• Chemical Name: (2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal
• CAS No.: 3615-41-6
• Deprecated CAS: 4469-18-5,39665-53-7,2497593-58-3,39665-53-7
• Molecular Formula: C6H12O5
• Molecular Weight: 164.158
• Hs Code.: 2912491000
• European Community (EC) Number: 222-793-4
• UNII: QN34XC755A
• DSSTox Substance ID: DTXSID7042647
• Nikkaji Number: J8.185J
• Wikipedia: Rhamnose
• Wikidata: Q414109
• Metabolomics Workbench ID: 50358
• Mol file: 3615-41-6.mol

Synonyms:Deoxymannose;Rhamnose;Rhamnose, L Isomer;Rhamnose, L-Isomer

Chemical Property of (2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 1.1E-11mmHg at 25°C
• Melting Point: 91-95 °C
• Refractive Index: 1.6400 (estimate)
• Boiling Point: 399.1 °C at 760 mmHg
• PKA: 12.50±0.20(Predicted)
• Flash Point: 209.3 °C
• PSA: 90.15000
• Density: 1.41 g/cm³
• LogP: -2.19380
• Storage Temp.: 2-8°C
• Water Solubility.: 521.5g/L(40 oC)
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 164.06847348
• Heavy Atom Count: 11
• Complexity: 126

Purity/Quality:

99% ^*data from raw suppliers

L-Rhamnose natural sourced, 99%, FG ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C(C(C(C=O)O)O)O)O
• Isomeric SMILES: C[C@@H]([C@@H]([C@H]([C@H](C=O)O)O)O)O
• Uses: Synthetic sweetener research.

Technology Process of (2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal

There total 1034 articles about (2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.0%

C23H22O12 → 3-hydroxy-2,7,8-trimethoxychromeno[5,4,3-cde]chromene-5,10-dione (5145-53-9) + L-Rhamnose (3615-41-6,478518-52-4)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 80 ℃; for 1h;

DOI:10.1007/s11418-017-1137-y

Reference yield:

trilliumoside I → D-apiose (639-97-4,6477-44-7,42927-70-8) + L-arabinose (5328-37-0) + L-Rhamnose (3615-41-6,478518-52-4)

Guidance literature:

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

DOI:10.1016/j.phytochem.2019.112125

Reference yield:

kaempferol-3-O-α-L-rhamnosyl-(1'''→6'')-O-β-D-galactopyranosyl-7-O-β-D-apiofuranoside → D-apiose (639-97-4,6477-44-7,42927-70-8) + L-Rhamnose (3615-41-6,478518-52-4) + D-Galactose (59-23-4)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; water; at 90 ℃; for 2h;

DOI:10.1080/10286020.2013.823951

upstream raw materials:

(2S,3S,4S,5S,6R)-2-methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol

C₄₇H₆₁NO₂₇

pseudo-ginsenoside-RS₁

sulfuric acid

Downstream raw materials:

methyl 6-deoxy-α-L-mannopyranoside

D,L-rhamnose

L-idomethylonic acid

4-α-L-rhamnopyranosylamino-benzoic acid

Refernces

• 1、 Huang, An-Cheng,Wilde, Amelie,Ebmeyer, Johanna,Skouroumounis, George K.,Taylor, Dennis K.. "Examination of the phenolic profile and antioxidant activity of the leaves of the australian native plant smilax glyciphylla". . p. 1930 - 1936. Retrieved 2013.
• 2、 Abdelmohsen, Usama Ramadan,Hajjar, Dina,Hamed, Ashraf Nageeb Elsayed,Kamel, Mohamed Salah,Mahmoud, Basma Khalaf,Matsunami, Katsuyoshi,Samy, Mamdouh Nabil,Sugimoto, Sachiko,Yamano, Yoshi. "Bignanoside A “A new neolignan glucoside” and bignanoside B “A new iridoid glucoside” from Bignonia binata leaves". . p. 200 - 205. Retrieved 2020.
• 3、 Xu, Min,Zhang, Ming,Wang, Dong,Yang, Chong-Ren,Zhang, Ying-Jun. "Phenolic compounds from the whole plants of Gentiana rhodantha (Gentianaceae)". . p. 1891 - 1900. Retrieved 2011.
• 4、 Han, Fubo,Lee, Ik-Soo. "A new flavonol glycoside from the aerial parts of Epimedium koreanum Nakai". . p. 320 - 325. Retrieved 2017.
• 5、 Ko, Hae Ju,Lee, Joo Hee,Kim, Yeong Shik,Lee, Je Hyun,Woo, Eun-Rhan. "A new triterpene glycoside from the stems of Akebia quinata". . p. 356 - 359. Retrieved 2015.
• 6、 Zhao, Zhimin,Matsunami, Katsuyoshi,Otsuka, Hideaki,Shinzato, Takakazu,Takeda, Yoshio. "Tareciliosides H-M: Further cycloartane glycosides from leaves of Tarenna gracilipes". . p. 902 - 905. Retrieved 2011.
• 7、 Sarikahya, Nazli Boeke,Kirmiziguel, Sueheyla. "Novel biologically active glycosides from the aerial parts of Cephalaria gazipashensis". . p. 323 - 334. Retrieved 2012.
• 8、 Li, Dan,Liu, Hui,Ni, Wei,Xiao, Wei-Lie,He, Li,Guo, Zhen-Yu,Qin, Xu-Jie,Liu, Hai-Yang. "Molecular networking-based strategy for the discovery of polyacetylated 18-norspirostanol saponins from Trillium tschonoskii maxim.". . . Retrieved 2019.
• 9、 Yang, Bing-You,Yin, Xin,Liu, Yan,Zhao, Dong-Ying,Kuang, Hai-Xue. "New steroidal saponins from the roots of Solanum melongena L.". . p. 12 - 19. Retrieved 2018.
• 10、 Srinroch, Chutima,Sahakitpichan, Poolsak,Techasakul, Supanna,Chimnoi, Nitirat,Ruchirawat, Somsak,Kanchanapoom, Tripetch. "Benzyl and phenylethanoid glycosides from the leaves of Magnolia sirindhorniae". . p. 205 - 209. Retrieved 2019.