89-67-8

Basic information

• Product Name: D-glycero-D-gulo-heptono-1,4-lactone
• Synonyms: D-glycero-D-gulo-heptono-1,4-lactone;α-D-Glucoheptonic γ-lactone, D-Glycero-D-guloheptono-γ-lactone;(3R,4S,5S)-3,4-Dihydroxy-5-[(1R,2R)-1,2,3-trihydroxypropyl]tetrahydrofuran-2-one;(5S)-5-[(1R,2R)-1,2,3-Trihydroxypropyl]-3α,4α-dihydroxytetrahydrofuran-2-one;3α,4α-Dihydroxy-5α-[(1R,2R)-1,2,3-trihydroxypropyl]-4,5-dihydrofuran-2(3H)-one;D-glycero-D-gulo-Heptonic acid γ-lactone;Einecs 201-929-6;D-Glycero-D-gulo-heptonic acid gamma-lactone
• CAS NO: 89-67-8
• Molecular Formula: C₇H₁₂O₇
• Molecular Weight: 208.16598
• EINECS: 201-929-6
• Mol File: 89-67-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 152-155 °C(lit.)
• Boiling Point: 461°C at 760 mmHg
• Flash Point: 192.1°C
• Appearance: /
• Density: 1.61g/cm³
• Vapor Pressure: 1.94E-10mmHg at 25°C
• Refractive Index: 1.565
• PKA: 12.05±0.60(Predicted)
• CAS DataBase Reference: D-glycero-D-gulo-heptono-1,4-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: D-glycero-D-gulo-heptono-1,4-lactone(89-67-8)
• EPA Substance Registry System: D-glycero-D-gulo-heptono-1,4-lactone(89-67-8)

Safety Data

• Hazardous Substances Data: 89-67-8(Hazardous Substances Data)

Usage

Uses

γ-?Lactone D-?Glycero-?D-?gulo-?Heptonic Acid can be used for sunscreen anti-aging repair lotion.

InChI:InChI=1/C7H12O7/c1-13-7-4(10)2(8)3(9)5(14-7)6(11)12/h2-5,7-10H,1H3,(H,11,12)

Synthetic route

5,7-O-benzylidene-D-glycero-D-gulo-heptono-1,4-lactone (151795-04-9) → α-D-glucoheptonic γ-lactone (89-67-8)

Conditions	Yield
With acetic acid for 24h; Ambient temperature;	95%

D-glucoheptonic acid (87-74-1) → α-D-glucoheptonic γ-lactone (89-67-8)

D-glycero-D-gulo-heptonic acid hydrazide (130538-63-5) → α-D-glucoheptonic γ-lactone (89-67-8)

Conditions	Yield
With hydrogenchloride; nitrogen oxides

D-glucose (50-99-7) → α-D-glucoheptonic γ-lactone (89-67-8)

Conditions	Yield
ueber das Calcium-Salz der D-glycero-D-gulo-Heptonsaeure;

D-glycero-D-gulo-heptonic benzoylhydrazide (77364-17-1) → α-D-glucoheptonic γ-lactone (89-67-8)

Conditions	Yield
With copper(II) sulfate 1.) water, reflux 5 h; Multistep reaction;
With hydrogenchloride; nitrous anhydride In ethanol; water at 15 - 20℃; for 3h; bubbling nitrous anhydride;

4,6-O-benzylidene-D-glucose (3006-41-5, 20771-09-9, 25152-90-3, 97232-16-1, 104022-77-7, 113566-67-9, 113566-68-0) → α-D-glucoheptonic γ-lactone (89-67-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) NaHCO3, 2.) H2O, 3.) AcOH 2: 95 percent / 80percent aq. AcOH / 24 h / Ambient temperature View Scheme

acetone (67-64-1) + α-D-glucoheptonic γ-lactone (89-67-8) → Mono-O-isopropyliden-heptono-γ-lacton (14548-94-8)

Conditions	Yield
With copper(II) sulfate	99%

benzaldehyde (100-52-7) + α-D-glucoheptonic γ-lactone (89-67-8) → 3,5(R)-O-benzylidene-D-glycero-D-gulo-heptono-1,4-lactone (151794-98-8)

Conditions	Yield
With hydrogenchloride In water at 20℃; for 2h;	96%
With hydrogenchloride for 2h; Ambient temperature;	91%

acetic anhydride (108-24-7) + α-D-glucoheptonic γ-lactone (89-67-8) → 2,3,5,6,7-penta-O-acetyl-D-glycero-D-gulo-heptono-1,4-lactone (114682-37-0)

Conditions	Yield
With perchloric acid for 2h;	95%
With perchloric acid for 0.5h; Ambient temperature;	92%

α-D-glucoheptonic γ-lactone (89-67-8) → D-glycero-D-gulo-heptose (3146-50-7)

Conditions	Yield
With sodium tetrahydroborate; Amberlite IR-120 H(+) In water at 0℃; for 1h; pH=3 - 5;	94.9%
durch elektrochemische Reduktion (Quecksilber-Kathode) in wss. Schwefelsaeure;
With sulfuric acid Reduktion an Quecksilber-Kathoden;
With sodium borate; sulfuric acid
With sodium amalgam; sulfuric acid

acetone (67-64-1) + α-D-glucoheptonic γ-lactone (89-67-8) → 3,5:6,7-bis-O-(1-methylethylidene)-α-D-glucoheptonic γ-lactone (6605-22-7)

Conditions	Yield
With iodine	86.5%
With iodine for 0.5h;	86.5%
With phosphoric acid; zinc(II) chloride for 24h; Ambient temperature;	66%

acetone (67-64-1) + α-D-glucoheptonic γ-lactone (89-67-8) → 3,5:6,7-bis-O-(1-methylethylidene)-α-D-glucoheptonic γ-lactone

Conditions	Yield
With iodine for 0.333333 - 0.5h;	86.5%

α-D-glucoheptonic γ-lactone (89-67-8) → <1,1-2H2>-D-glycero-D-gulo-heptitol

Conditions	Yield
With sodium borodeuteride; cation-exchange resin	80%

Thiocarbohydrazide (2231-57-4) + α-D-glucoheptonic γ-lactone (89-67-8) → 4-amino-3-(D-glucoheptonic-hexitol-1-yl)-1H-1,2,4-triazole-5-thione (219474-93-8)

Conditions	Yield
With pyridine for 4h; Heating;	80%

α-D-glucoheptonic γ-lactone (89-67-8) → (2R,3R,4R,5S,6S)-Heptane-1,2,3,4,5,6,7-heptaol (488-38-0, 527-06-0, 608-61-7, 1068-96-8, 1068-99-1, 1069-00-7, 1186-95-4, 1186-96-5, 2204-11-7, 3343-95-1, 6893-83-0, 30635-52-0, 30636-42-1, 30636-43-2, 60046-24-4, 61091-63-2, 61091-66-5, 68108-40-7, 68108-41-8, 68108-42-9, 84924-59-4)

Conditions	Yield
With cation-exchange resin; borohydride	76%
With sodium borate; water; boric acid unter Zusatz eines sauren Kationen-Austauschers und anschliessenden Behandeln mit wss.Natronlauge;
With sodium borate; water; boric acid unter Zusatz eines sauren Kationen-Austauschers und anschliessenden Behandeln mit Natriumboranat in Aethanol unter Zusatz von Aluminium;

Thiocarbohydrazide (2231-57-4) + α-D-glucoheptonic γ-lactone (89-67-8) → 4-amino-3-(D=glycero-D-gulo-pentitol-1-yl)-5-mercapto-1,2,4-triazole (219474-93-8)

Conditions	Yield
With pyridine Heating;	71%

2,2-dimethoxy-propane (77-76-9) + α-D-glucoheptonic γ-lactone (89-67-8) → 3,5:6,7-bis-O-(1-methylethylidene)-α-D-glucoheptonic γ-lactone (6605-22-7) + 2,3:6,7-Di-O-isopropyliden-D-glycero-D-guloheptonono-γ-lacton (14548-95-9)

Conditions	Yield
With toluene-4-sulfonic acid In acetone at 20℃; for 18h;	A 70% B 12%
With sulfuric acid In acetone at 0℃; for 8h; Inert atmosphere; regioselective reaction;	A 57.7% B n/a

cyclopentanone (120-92-3) + α-D-glucoheptonic γ-lactone (89-67-8) → 3,5:6,7-di-O-cyclopentylidene-D-glycero-D-gulo-heptono-γ-lactone (223534-22-3)

Conditions	Yield
With phosphoric acid; zinc(II) chloride for 24h; Ambient temperature;	69%

acetone (67-64-1) + α-D-glucoheptonic γ-lactone (89-67-8) → 3,5:6,7-bis-O-(1-methylethylidene)-α-D-glucoheptonic γ-lactone (6605-22-7) + 2,3:6,7-Di-O-isopropyliden-D-glycero-D-guloheptonono-γ-lacton (14548-95-9)

Conditions	Yield
With phosphoric acid; zinc(II) chloride for 24h; Ambient temperature;	A 66% B 7%
With phosphoric acid; zinc(II) chloride for 24h; Ambient temperature;	A 66% B 7%
With calcium sulfate; toluene-4-sulfonic acid at 150℃; for 1.5h;	A 38% B 25%

p-toluenesulfonyl chloride (98-59-9) + α-D-glucoheptonic γ-lactone (89-67-8) → 2,7-di-O-tosyl-D-glycero-D-gulo-heptono-1,4-lactone (146820-62-4)

Conditions	Yield
With pyridine In acetone at 0℃; for 3h;	64%

pentan-3-one (96-22-0) + α-D-glucoheptonic γ-lactone (89-67-8) → (3aR,6S,6aR)-6-[(R)-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2,2-diethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one (158348-12-0)

Conditions	Yield
With sulfuric acid	55%
With sulfuric acid at 22℃;	43%

tert-butylchlorodiphenylsilane (58479-61-1) + α-D-glucoheptonic γ-lactone (89-67-8) → 7-O-tert-butyldiphenylsilyl-D-glycero-D-gulo-heptono-1,4-lactone (129415-28-7) + 2,7-di-O-tert-butyldiphenylsilyl-D-glycero-D-gulo-heptono-1,4-lactone (129415-29-8)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide 1) 0 deg C --> room temperature, 3 h, 2) 22 h;	A 55% B 18%

2,2,2-Trichloroethyldecanoylate (84443-55-0) + α-D-glucoheptonic γ-lactone (89-67-8) → Decanoic acid (2R,3R)-3-((2S,3S,4R)-3,4-dihydroxy-5-oxo-tetrahydro-furan-2-yl)-2,3-dihydroxy-propyl ester

Conditions	Yield
With pyridine for 144h; Ambient temperature; porcine pancreatic lipase;	54.5%

benzoyl chloride (98-88-4) + α-D-glucoheptonic γ-lactone (89-67-8) → 2,5,6,7-tetra-O-benzoyl-3-deoxy-D-arabino-hept-2-enono-1,4-lactone (41356-09-6)

Conditions	Yield
With pyridine for 8h;	50%

α-D-glucoheptonic γ-lactone (89-67-8) → 2,7-dibromo-2,7-dideoxy-D-glycero-D-ido-heptono-1,4-lactone (116386-12-0)

Conditions	Yield
With hydrogen bromide In acetic acid for 1h;	46%
With hydrogen bromide; acetic acid for 1h; enantiospecific reaction;

pentan-3-one (96-22-0) + α-D-glucoheptonic γ-lactone (89-67-8) → (3aR,6S,6aR)-6-[(R)-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2,2-diethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one (158348-12-0) + (3R,4S,5R)-5-[(R)-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-3,4-dihydroxy-dihydro-furan-2-one (286931-17-7)

Conditions	Yield
With sulfuric acid at 20℃; for 72h; Condensation; ketalization;	A 39% B 39%

1,2-diamino-benzene (95-54-5) + α-D-glucoheptonic γ-lactone (89-67-8) → 2-(D-glycero-D-gulohexahydroxyhexyl)benzimidazole (20188-65-2)

Conditions	Yield
In ethanol at 100℃; for 24h;	20%
With water

acetic anhydride (108-24-7) + α-D-glucoheptonic γ-lactone (89-67-8) → O2,O3,O5,O6-tetraacetyl-D-glycero-D-gulo-heptonic acid-4-lactone

α-D-glucoheptonic γ-lactone (89-67-8) + Quinine (130-95-0) → quinine; D-glycero-D-gulo-heptonate

Conditions	Yield
With ethanol

α-D-glucoheptonic γ-lactone (89-67-8) + Quinine (130-95-0) → quinine; D-glycero-D-gulo-heptonate

Conditions	Yield
With ethanol

α-D-glucoheptonic γ-lactone (89-67-8) + methyl iodide (74-88-4) → O2,O3,O5,O6,O7-pentamethyl-D-glycero-D-gulo-heptonic acid-lactone (108844-68-4)

Conditions	Yield
With methanol; silver(l) oxide

α-D-glucoheptonic γ-lactone (89-67-8) → 4-propylbutanolide (105-21-5)

Conditions	Yield
With phosphorus; hydrogen iodide

Upstream product

• 2595-97-3 D-Allose 
• 143-33-9 sodium cyanide 
• 87-74-1 D-glucoheptonic acid 
• 130538-63-5 D-glycero-D-gulo-heptonic acid hydrazide 
• 50-99-7 D-glucose 
• 77364-17-1 D-glycero-D-gulo-heptonic benzoylhydrazide 
• 3006-41-5 4,6-O-benzylidene-D-glucose 
• 151795-04-9 5,7-O-benzylidene-D-glycero-D-gulo-heptono-1,4-lactone 

Downstream Products

• 1194755-26-4 D-glycero-D-allo-heptonic acid-(N'-phenyl-hydrazide) 
• 20188-65-2 2--benzimidazol 
• 105-21-5 4-propylbutanolide 
• 3146-50-7 D-glycero-D-gulo-heptose 
• 1426682-75-8 C₁₄H₁₄O₄ 
• 1425495-11-9 C₁₄H₁₆O₄S 
• 1425495-12-0 C₁₅H₁₈O₆S₂ 
• 1425495-13-1 C₁₄H₁₅N₃O₃S 
• 78518-27-1 3-Chloro-benzoic acid N'-((2R,3R,4S,5R,6R)-2,3,4,5,6,7-hexahydroxy-heptanoyl)-hydrazide 
• 78518-26-0 2-Chloro-benzoic acid N'-((2R,3R,4S,5R,6R)-2,3,4,5,6,7-hexahydroxy-heptanoyl)-hydrazide 
• 78518-29-3 4-Bromo-benzoic acid N'-((2R,3R,4S,5R,6R)-2,3,4,5,6,7-hexahydroxy-heptanoyl)-hydrazide 
• 78530-01-5 (2R,3R,4S,5R,6R)-2,3,4,5,6,7-Hexahydroxy-heptanoic acid N'-(4-iodo-phenyl)-hydrazide 
• 78518-23-7 (2R,3R,4S,5R,6R)-2,3,4,5,6,7-Hexahydroxy-heptanoic acid N'-(4-bromo-phenyl)-hydrazide 
• 78518-25-9 (2R,3R,4S,5R,6R)-2,3,4,5,6,7-Hexahydroxy-heptanoic acid N'-p-tolyl-hydrazide 

Relevant articles and documents

BENZYLIDENE ACETALS OF HEPTONOLACTONES

The preparation of 3,5-(R)-O-benzylidene-D-glycero-D-gulo-heptono-1,4-lactone, a readily available and powerful chiron, is described; other benzylidene derivatives of heptono-1,4-lactones are characterised.The X-ray crystal structure of 3,5(R):6,7(R)-di-O-benzylidene-D-glycero-D-gulo-heptono-1,4-lactone is reported.