D-RIBOSE

D-Ribose is a naturally occurring pentose sugar that plays a central role in ATP production and cellular energy metabolism.
D-Ribose is widely used in dietary supplements and sports nutrition products to support energy levels, reduce fatigue, and enhance recovery.
D-Ribose is highly soluble and easily incorporated into various formulations, making it a versatile ingredient in food, pharmaceutical, and nutraceutical applications.

CAS number: 50-69-1
EC number: 200-059-4
Molecular Formula: C5H10O5
Molecular weight: 150.13 g/mol

Synonyms: D-ribopyranose, (3R,4R,5R)-Oxane-2,3,4,5-tetrol, Ribopyranose, D Ribose, D-Rib, ribopyranoside, d-ribopyranoside, CHEBI:47013, SNFG:Rib, D-alpha-ribofuranoside, Rib (SNFG), RefChem:53254, GlyTouCan:G75380KK, CHEBI:16988, CHEBI:33942, CHEBI:47007, G75380KK, 200-059-4, (3R,4S,5R)-5-(hydroxymethyl)tetrahydrofuran-2,3,4-triol, 50-69-1, 681HV46001, D-ribo-2,3,4,5-tetrahydroxyvaleraldehyde, D-Ribose, DTXCID4023917, DTXSID6043917, FEMA NO. 3793, Rib, Ribo-2,3,4,5-tetrahydroxyvaleraldehyde, D-, Ribose, Ribose, D-, RIBOXYL, 10257-32-6, (3R,4R,5R)-Tetrahydro-2H-pyran-2,3,4,5-tetraol, 10257-33-7, CHEBI:47006, (3R,4R,5R)-tetrahydro-2H-pyran-2,3,4,5-tetrol, Ribopyranose (7CI,8CI,9CI), Ribiose, Epitope ID:149136, Epitope ID:581504, EC 700-481-3, Ribopyranose(7ci,8ci,9ci), SCHEMBL339948, DTXSID70450356, SRBFZHDQGSBBOR-SOOFDHNKSA-N, EBC-44259, NS00106195, C21057, R-5500, RIBONIC ACID-Gamma-LACTONE, D-(+)-(RG), EN300-1704373, Q27120754

D-Ribose is a naturally occurring pentose sugar that plays a critical role in cellular energy metabolism.
D-Ribose is a key structural component of ATP (adenosine triphosphate), RNA, and other essential biomolecules.
Due to its involvement in energy production, D-Ribose is widely used in nutraceutical, pharmaceutical, and food applications, particularly in products targeting energy support and recovery.

D-Ribose is a simple sugar molecule produced in the body and consumed through food and supplements.
D-Ribose is a natural component of DNA and RNA.

D-Ribose is also a key member of adenosine triphosphate (ATP), the main energy source for recording information.
D-Ribose plays a vital role in energy production, enabling muscle contraction, nerve impulse execution, protein synthesis, intracellular signaling, and many other biological processes.

While the body naturally produces D-Ribose, a supportive exercise regimen can support cardiovascular function, muscle function, and more.

Ribose is a simple sugar and carbohydrate with molecular formula C5H10O5 and the linear-form composition H−(C=O)−(CHOH)4−H.
The naturally occurring form, D-Ribose, is a component of the ribonucleotides from which RNA is built, and so this compound is necessary for coding, decoding, regulation and expression of genes.

D-Ribose has a structural analog, deoxyribose, which is a similarly essential component of DNA.
L-Ribose is an unnatural sugar that was first prepared by Emil Fischer and Oscar Piloty in 1891.

D-Ribose was not until 1909 that Phoebus Levene and Walter Jacobs recognised that D-Ribose was a natural product, the enantiomer of Fischer and Piloty's product, and an essential component of nucleic acids.
Fischer chose the name "ribose" as D-Ribose is a partial rearrangement of the name of another sugar, arabinose, of which ribose is an epimer at the 2' carbon; both names also relate to gum arabic, from which arabinose was first isolated and from which they prepared L-Ribose.

Like most sugars, ribose exists as a mixture of cyclic forms in equilibrium with its linear form, and these readily interconvert especially in aqueous solution.
The name "ribose" is used in biochemistry and biology to refer to all of these forms, though more specific names for each are used when required.

In its linear form, ribose can be recognised as the pentose sugar with all of its hydroxyl functional groups on the same side in its Fischer projection.
D-Ribose has these hydroxyl groups on the right hand side and is associated with the systematic name (2R,3R,4R)-2,3,4,5-tetrahydroxypentanal, whilst L-Ribose has its hydroxyl groups appear on the left hand side in a Fischer projection.

Cyclisation of ribose occurs via hemiacetal formation due to attack on the aldehyde by the C4' hydroxyl group to produce a furanose form or by the C5' hydroxyl group to produce a pyranose form.
In each case, there are two possible geometric outcomes, named as α- and β- and known as anomers, depending on the stereochemistry at the hemiacetal carbon atom (the "anomeric carbon").
At room temperature, about 76% of D-Ribose is present in pyranose forms: 228  (α:β = 1:2) and 24% in the furanose forms: 228  (α:β = 1:3) with only about 0.1% of the linear form present.

The ribonucleosides adenosine, cytidine, guanosine, and uridine are all derivatives of β- d-ribofuranose.
Metabolically important species that include phosphorylated ribose include ADP, ATP, coenzyme A: 228–229  and NADH.

cAMP and cGMP serve as secondary messengers in some signaling pathways and are also ribose derivatives.
The ribose moiety appears in some pharmaceutical agents, including the antibiotics neomycin and paromomycin.

D-Ribose is an aldopentose monosaccharide.
D-Ribose is phosphorylated into D-Ribose 5-phosphate by ribokinase and then supports the synthesis of tryptophan and histidine.

Additionally, D-Ribose 5-phosphate is part of the pentose phosphate pathway.
D-Ribose may be used as a cell culture media supplement.

Uses of D-Ribose:
D-Ribose is widely used in dietary supplements, sports nutrition, pharmaceutical formulations, and functional foods due to its central role in cellular energy production.
D-Ribose supports ATP synthesis, making it valuable in products aimed at improving energy levels, reducing fatigue, and enhancing physical performance and recovery.

In the pharmaceutical and medical nutrition fields, D-Ribose is utilized for cardiovascular support and in conditions associated with impaired energy metabolism.
Additionally, D-Ribose is incorporated into energy drinks and fortified foods as a functional ingredient to promote overall metabolic efficiency.

Dietary Supplements:
D-Ribose is used to support cellular energy production and ATP synthesis.

Sports Nutrition:
D-Ribose is included in performance and recovery products to reduce fatigue and improve endurance.

Pharmaceutical Applications:
D-Ribose is utilized in formulations targeting energy metabolism and cardiovascular support.

Functional Foods & Beverages:
D-Ribose is incorporated into energy drinks and fortified foods.

Medical Nutrition:
D-Ribose is used in clinical nutrition products for patients with energy deficiencies.

Benefits of D-Ribose:

D-Ribose supplementation offers a range of potential health benefits, including:

Support for heart health:
Relief from symptoms of fibromyalgia and chronic fatigue syndrome
Improved muscle function
Faster exercise recovery

May Boost Energy Production:
As the body ages, D-Ribose produces less ATP, and the ATP decline is related to the health of our mitochondria.
When mitochondria produce less ATP, symptoms can include fatigue and lack of energy, exercise intolerance, and muscle weakness.

The good news is that there are natural lifestyle habits, nutrition, and supplements that can support ATP levels.
D-Ribose is the main building block for ATP.
While the body naturally produces D-Ribose, it can also be consumed as a supplement in tablet or powder form.

Additional ways to support mitochondrial health include eating antioxidant-rich foods like blueberries, pomegranate seeds, and dark chocolate, exercising regularly, prioritizing sleep, stress management, and supplements tailored to your health needs.

While scientific evidence supporting the benefits of D-Ribose is limited, some studies suggest that D-Ribose may help increase energy production by enhancing ATP recovery when mitochondrial function is compromised.

May Accelerate Exercise Recovery:
D-Ribose can help reduce soreness and aid in faster muscle recovery after exercise by assisting in the recovery of ATP levels in muscles.
Studies show that consuming 15 grams of D-Ribose before and after exercise can reduce muscle soreness and improve the healing of muscle damage.
In addition to D-Ribose, pre- and post-exercise nutrition plays a crucial role in muscle recovery.

Pre-exercise nutrition should focus on easily digestible carbohydrates along with some protein for sustained energy.
Post-exercise nutrition should focus on protein for muscle recovery along with carbohydrates to replenish glycogen levels.

Glycogen is glucose stored in muscles and serves as an immediate energy source for exercise and physical activity.
Additional nutrients and supplements that can support exercise recovery include protein powders, omega-3 fatty acids, electrolytes, vitamin C, and vitamin D.

May Support Heart Health:
D-Ribose may also improve heart health by supporting ATP production and heart function.
An older review of studies found that D-Ribose may improve quality of life and allow people with congestive heart failure or coronary artery disease to exercise for longer periods with fewer symptoms.5

Additional supplements that may support heart health include omega-3 fatty acids, magnesium, and CoQ10.
Beyond supplements, natural remedies for a healthy heart include proper nutrition and healthy lifestyle habits.
A whole-food diet rich in antioxidant-rich fruits and vegetables, quality sleep, stress management, and regular exercise, as well as avoiding smoking and alcohol consumption, are key to supporting heart health.

May Relieve Fibromyalgia Symptoms:
D-Ribose may help reduce symptoms of fibromyalgia and chronic fatigue syndrome.
A small, older study found that taking 15 grams of D-Ribose helped improve pain intensity, energy, mental clarity, and sleep in those with chronic fatigue syndrome or fibromyalgia.
While more research is needed to understand the benefits of D-Ribose for specific pain disorders and chronic fatigue, current research is promising.

Production of D-Ribose:
D-Ribose is primarily produced through microbial fermentation using selected strains such as Bacillus subtilis or Candida species.
In this process, carbohydrate sources like glucose are metabolized via the pentose phosphate pathway to generate ribose.

After fermentation, the broth is clarified to remove cells and impurities, followed by purification steps such as ion-exchange and crystallization.
The purified D-Ribose is then concentrated, dried, and milled into a stable crystalline powder suitable for food, pharmaceutical, and nutraceutical applications.

Synthesis of D-Ribose:
D-Ribose can be synthesized chemically or biotechnologically.
In chemical synthesis, D-Ribose is obtained through the degradation or transformation of larger carbohydrate molecules, although this route is less common industrially due to complexity and low selectivity.
The more widely used method is biotechnological synthesis, where D-Ribose is produced via microbial pathways involving the conversion of glucose through the pentose phosphate pathway.

In this route, microorganisms convert glucose into ribose-5-phosphate, which is subsequently dephosphorylated to yield D-Ribose.
This approach offers higher efficiency, better stereochemical control, and is more suitable for large-scale industrial production.

Stability and Reactivity of D-Ribose:

Chemical stability:
Stable under normal conditions of use, handling, and storage.

Reactivity:
No hazardous reactions under normal conditions.

Conditions to avoid:
Excessive heat.
Moisture.
Strong oxidizing environments.

Incompatible materials:
Strong oxidizing agents.

Hazardous decomposition products:
Carbon oxides (CO, CO₂) may form upon thermal decomposition.

Handling and Storage of D-Ribose:

Handling:
Avoid dust formation.
Avoid inhalation of dust.
Use appropriate ventilation.
Follow standard hygiene practices.

Storage:
Store in a cool, dry, well-ventilated area.

Storage conditions:
Keep container tightly closed.
Protect from moisture.

Packaging materials:
Store in sealed, food-grade compatible containers.

Shelf life:
Approximately 24 months under recommended conditions.

First Aid Measures of D-Ribose:

Inhalation:
Move to fresh air.
Seek medical attention if irritation persists.

Skin contact:
Wash with soap and water.

Eye contact:
Rinse cautiously with water for several minutes.

Ingestion:
Rinse mouth.
Seek medical advice if discomfort occurs.

Firefighting Measures of D-Ribose:

Suitable extinguishing media:
Water spray.
Foam.
Dry chemical.
Carbon dioxide (CO₂).

Hazards:
Dust may form explosive mixtures in air.
Combustion may produce irritating fumes.

Protective equipment:
Firefighters should wear appropriate protective gear.
Use breathing apparatus.

Accidental Release Measures of D-Ribose:

Personal precautions:
Avoid dust inhalation.
Avoid contact with eyes.

Spill response:
Sweep or vacuum material.
Collect in suitable containers.

Environmental precautions:
Prevent release into drains and waterways.

Cleanup methods:
Dispose according to local regulations.

Exposure Controls / Personal Protection of D-Ribose:

Respiratory protection:
Use dust mask if airborne particles are present.

Eye protection:
Use safety glasses or goggles.

Skin protection:
Wear protective gloves.

Hygiene measures:
Wash hands after handling.
Avoid eating or drinking during use.

Engineering controls:
Ensure adequate ventilation.

Identifiers of D-Ribose:
CAS Number: 50-69-1
ChEMBL: ChEMBL1159662
ChemSpider: 4470639 aldehydo form D-(−)-Ribose
DrugBank: DB01936
EC Number: 200-059-4
PubChem CID: 5779
5311110 aldehydo form D-(−)-Ribose
UNII: 681HV46001
InChI: aldehydo form D-(−)-Ribose: InChI=1/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4+,5-/m0/s1
Key: PYMYPHUHKUWMLA-LMVFSUKVBD
Aldehydo form D-(−)-Ribose: InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4+,5-/m0/s1
Key: PYMYPHUHKUWMLA-LMVFSUKVSA-N
SMILES: aldehydo form D-(−)-Ribose: C([C@H]([C@H]([C@H](C=O)O)O)O)O

Molecular Formula: C5H10O5
Molecular weight: 150.13 g/mol
CAS number: 50-69-1
EC number: 200-059-4
Chemical family: Monosaccharide (aldopentose)
Origin: Natural

Properties of D-Ribose:
Chemical formula: C5H10O5
Molar mass: 150.13
Appearance: White solid
Melting point: 95 °C (203 °F; 368 K)
Solubility in water: 100 g/L (25 °C, 77 °F)
Chiral rotation ([α]D): −21.5° (H2O)

Appearance: White crystalline powder
Odor: Odorless
Taste: Sweet
Physical state: Solid
Solubility: Highly soluble in water
Melting point: ~87–90°C
Density: ~1.6 g/cm³
pH: Neutral to slightly acidic
Stability: Stable under normal conditions

Molecular Weight: 150.13 g/mol
XLogP3-AA: -2.5
Hydrogen Bond Donor Count: 4
Hydrogen Bond Acceptor Count: 5
Rotatable Bond Count: 0
Exact Mass: 150.05282342 Da
Monoisotopic Mass: 150.05282342 Da
Topological Polar Surface Area: 90.2 Ų
Heavy Atom Count: 10
Complexity: 117
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 3
Undefined Atom Stereocenter Count: 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Specifications of D-Ribose:
Catalog ID: R-600
CAS #: 50-69-1
Formula: C5H10O5
MW: 150.13 g/mol
Storage/handling: Store at 4°C.

Related compounds of D-Ribose:
Deoxyribose

Related aldopentoses:
Arabinose
Xylose
Lyxose

Names of D-Ribose:

IUPAC names:
D-Ribose
d-ribo-Pentose

Systematic IUPAC name:
(2R,3R,4S,5R)-5-(hydroxymethyl)oxolane-2,3,4-triol

Other name:
D-Ribose